4613-71-2

Basic information

• Product Name: 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose
• Synonyms: 5-O-BENZOYL-1,2-DI-O-ACETYL-3-DEOXY-D-RIBOFURANOSE;5-O-BENZOYL-1,2-DI-O-ACETYL-3-DEOXY-D-RIBOSE;1,2-O-Di-O-acetyl-5-O-benzoyl-3-deoxy-D-ribofuranose;1,2-Di-O-Acetyl-5-O-benzoyl-3-deoxy-D-erythro-pentofuranose
• CAS NO: 4613-71-2
• Molecular Formula: C₁₆H₁₈O₇
• Molecular Weight: 322.31
• Mol File: 4613-71-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Refractive Index: 1.531
• CAS DataBase Reference: 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose(4613-71-2)
• EPA Substance Registry System: 5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose(4613-71-2)

Safety Data

• Hazardous Substances Data: 4613-71-2(Hazardous Substances Data)

Usage

Description

5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose is a complex organic compound that serves as an important intermediate in the synthesis of various biologically active molecules. It is characterized by its unique structure, which includes a ribofuranose core with specific functional groups that can be further modified or reacted to produce desired compounds.

Uses

Used in Pharmaceutical Industry:
5-O-Benzoyl-1,2-di-O-acetyl-3-deoxy-D-ribofuranose is used as a key reactant for the synthesis of aminooxopyridopyrimidine nucleosides, which possess antitumor cytotoxicity. These nucleosides are promising candidates for the development of new anticancer drugs, as they can potentially inhibit the growth and proliferation of cancer cells.
In the synthesis of these nucleosides, the compound's specific functional groups allow for the formation of essential chemical bonds and the introduction of bioactive moieties. This makes it a valuable component in the development of novel therapeutic agents for cancer treatment.
Additionally, the compound may also find applications in other areas of the pharmaceutical industry, such as the development of antiviral, antibacterial, or antifungal agents, due to its ability to be modified and reacted with various other molecules. However, further research and development would be required to explore these potential applications fully.

InChI:InChI=1/C16H18O7/c1-10(17)21-14-8-13(23-16(14)22-11(2)18)9-20-15(19)12-6-4-3-5-7-12/h3-7,13-14,16H,8-9H2,1-2H3/t13-,14+,16?/m0/s1

Synthetic route

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate (4105-29-7) + acetic anhydride (108-24-7) → 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2)

Conditions	Yield
Stage #1: [(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate With acetic acid for 2h; Heating; Stage #2: acetic anhydride With pyridine; dmap at 20℃; Further stages.;	80%
With sulfuric acid In acetic acid	52%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → 2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine (143653-60-5)

Conditions	Yield
With tin(IV) chloride In acetonitrile	93%

4-N-Acetylcytosine (14631-20-0) + 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 3'-deoxycytidine (7057-33-2)

Conditions	Yield
Stage #1: 4-N-Acetylcytosine; 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose With benzenesulfonamide In acetonitrile for 1h; Heating; Stage #2: With trimethylsilyl trifluoromethanesulfonate at 20℃; for 5h; Stage #3: With ammonium hydroxide In tetrahydrofuran; methanol at 50℃; for 6h; Further stages.;	90%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 2-O-acetyl-5-O-benzoyl-3-deoxy-β-D-erythro-pentofuranosyl azide

Conditions	Yield
With trimethylsilylazide; tin(IV) chloride In dichloromethane at 23℃; for 12h; azidation;	74%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + N6-isobutyrylaminocytosine (97626-98-7) → 2'-O-Acetyl-5'-O-benzoyl-4-N-isobutyryl-3'-deoxycytidine (159217-63-7)

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-ethane at 27℃; for 20h;	62%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + C6H2ClN5 (1343405-24-2) → C20H16ClN5O5 (1343405-28-6)

Conditions	Yield
With boron trifluoride diethyl etherate In acetonitrile for 1h; Reflux;	61%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + 5-methyltetrazole (4076-36-2) → Benzoic acid (2S,4R,5R)-4-acetoxy-5-(5-methyl-tetrazol-2-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
In ethylenediamine for 48h;	54%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + 2H-tetrazole (288-94-8) → Benzoic acid (2S,4R,5R)-4-acetoxy-5-tetrazol-2-yl-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
In ethylenediamine for 48h;	51%

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + N-(6,8-dioxo-7-(4-(trifluoromethyl)benzyl)-6,7,8,9-tetrahydro-1H-purin-2-yl)acetamide → ((2S,4R,5R)-5-(2-acetamido-6,8-dioxo-7-(4-(trifluoromethyl)benzyl)-1,6,7,8-tetrahydro-9H purin-9-yl)-4-acetoxytetrahydrofuran-2-yl)methyl benzoate

Conditions	Yield
Stage #1: 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose; N-(6,8-dioxo-7-(4-(trifluoromethyl)benzyl)-6,7,8,9-tetrahydro-1H-purin-2-yl)acetamide With N,O-bis-(trimethylsilyl)-acetamide In 1,2-dichloro-ethane at 80℃; for 0.5h; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 3h;	11%

(Ac)G(TMS)2 (42890-94-8) + 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → N2-acetyl-2'-O-acetyl-5'-O-benzoyl-3'-deoxyguanosine + Benzoic acid (2S,4R,5R)-4-acetoxy-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
Yield given. Yields of byproduct given;

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + 5-phenyl-2H-1,2,3,4-tetrazole (18039-42-4) → Benzoic acid (2S,4R,5R)-4-acetoxy-5-(5-phenyl-tetrazol-2-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
With tin(IV) chloride 1.) acetonitrile, 0 deg C, 1 h, 2.) 50 deg C, 2 h; Yield given. Multistep reaction;

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + 4-amino-8H-pyrido[2,3-d]pyrimidin-5-one (306960-30-5) → benzoic acid 4-acetoxy-5-(4-amino-5-oxo-5H-pyrido[2,3-d]pyrimidin-8-yl)-tetrahydro-furan-2-ylmethyl ester (1053253-53-4) + benzoic acid 4-acetoxy-5-(4-amino-5-oxo-5H-pyrido[2,3-d]pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
Stage #1: 4-aminopyrido[2,3-d]pyrimidin-5(8H)-one With N,O-bis-(trimethylsilyl)-acetamide In 1,2-dichloro-ethane at 75℃; for 2h; Stage #2: 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 72h; Vorbrueggen reaction; Heating; Further stages.;

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 4-amino-5-oxo-8-(3-deoxy-β-D-ribofuranosyl)pyrido[2,3-d]pyrimidine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 2 h / 75 °C 1.2: trimethylsilyl triflate / 1,2-dichloro-ethane / 72 h / Heating 2.1: NH3 / methanol / 20 h / 20 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → Benzoic acid (2S,4R,5S)-4-acetoxy-5-azido-tetrahydro-furan-2-ylmethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / Me3SiN3 / SnCl4 / CH2Cl2 / 12 h / 23 °C 2: SnCl4 / Me3SiOAc / CH2Cl2 / 192 h / 23 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 3'-deoxycytidine (7057-33-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / SnCl4 / 1,2-dichloro-ethane / 20 h / 27 °C 2: 98 percent / NH3 / methanol / 12 h / 25 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 4-(N-Isobutyryl)-3'-deoxycytidine (159217-64-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / SnCl4 / 1,2-dichloro-ethane / 20 h / 27 °C 2: 98 percent / NH3 / methanol / 12 h / 25 °C 3: 77 percent / dimethylformamide / 18 h / 25 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 4-(N-Isobutyryl)-5'-O-(4,4'-dimethoxytrityl)-3'-deoxycytidine (159217-65-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 62 percent / SnCl4 / 1,2-dichloro-ethane / 20 h / 27 °C 2: 98 percent / NH3 / methanol / 12 h / 25 °C 3: 77 percent / dimethylformamide / 18 h / 25 °C 4: 84 percent / pyridine / 24 h / 25 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 4-(N-Isobutyryl)-5'-O-(4,4'-dimethoxytrityl)-3'-deoxycytidine 2'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Conditions	Yield
Multi-step reaction with 5 steps 1: 62 percent / SnCl4 / 1,2-dichloro-ethane / 20 h / 27 °C 2: 98 percent / NH3 / methanol / 12 h / 25 °C 3: 77 percent / dimethylformamide / 18 h / 25 °C 4: 84 percent / pyridine / 24 h / 25 °C 5: 86 percent / diisopropylammonium tetrazolide / CH2Cl2 / 7 h / 25 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 3'-deoxy-5'-O-dimethoxytrityl-5-methyluridine (143653-61-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / SnCl4 / acetonitrile 2: 94 percent / K2CO3, MeOH / Heating 3: 81 percent / pyridine View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → Diisopropyl-phosphoramidous acid (2R,3R,5S)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (142103-12-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / SnCl4 / acetonitrile 2: 94 percent / K2CO3, MeOH / Heating 3: 81 percent / pyridine 4: 66 percent / iPr2NEt / tetrahydrofuran View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 3'-deoxy-5-methyluridine (7084-29-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / SnCl4 / acetonitrile 2: 94 percent / K2CO3, MeOH / Heating View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + C8H13N3O2Si → {(2S,4R,5R)-4-(acetyloxy)-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl]tetrahydro-2-furanyl}methyl benzoate (499785-77-2)

Conditions	Yield
With tin(IV) chloride In acetonitrile at 20℃; for 0.5h;

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) + 5-aminothaizolo<4,5-d>pyrimidine-2,7(3H,6H)-dione (30161-97-8) → [(2S,4R,5R)-4-acetoxy-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]methyl benzoate

Conditions	Yield
Stage #1: 5-aminothiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20 - 70℃; for 0.5h; Inert atmosphere; Stage #2: 5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 70℃; for 14h; Inert atmosphere;	5.7 g

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 5-amino-3-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]methyl benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 5-amino-3-[(2R,3R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C 3.1: 1H-imidazole / Petroleum ether; N,N-dimethyl-formamide / 2 h / 20 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → 5-amino-3-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-oxo-tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C 3.1: 1H-imidazole / Petroleum ether; N,N-dimethyl-formamide / 2 h / 20 °C 4.1: Dess-Martin periodane / tetrahydrofuran / 2 h / 20 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-phenoxycarbothioyloxy-tetrahydrofuran-2-yl]methyl benzoate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C 3.1: dmap / dichloromethane / 20 °C View Scheme

5-O-benzoyl-3-deoxy-1,2-di-O-acetyl-α,β-D-erythro-pentofuranose (4613-71-2) → [(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-(2-methylallyl)tetrahydrofuran-2-yl]methyl benzoate

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.5 h / 20 - 70 °C / Inert atmosphere 1.2: 14 h / 70 °C / Inert atmosphere 2.1: potassium carbonate / methanol / 3.5 h / 20 °C 3.1: dmap / dichloromethane / 20 °C 4.1: 2,2'-azobis(isobutyronitrile) / toluene / 4 h / 80 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere View Scheme

Upstream product

• 4105-29-7 [(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate 
• 108-24-7 acetic anhydride 

Downstream Products

• 1343405-28-6 C₂₀H₁₆ClN₅O₅ 
• 7057-33-2 3'-deoxycytidine 
• 499785-77-2 {(2S,4R,5R)-4-(acetyloxy)-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl]tetrahydro-2-furanyl}methyl benzoate 
• 142103-12-6 Diisopropyl-phosphoramidous acid (2R,3R,5S)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 143653-61-6 3'-deoxy-5'-O-dimethoxytrityl-5-methyluridine 
• 159217-65-9 4-(N-Isobutyryl)-5'-O-(4,4'-dimethoxytrityl)-3'-deoxycytidine 
• 1053253-53-4 benzoic acid 4-acetoxy-5-(4-amino-5-oxo-5H-pyrido[2,3-d]pyrimidin-8-yl)-tetrahydro-furan-2-ylmethyl ester 
• 159217-63-7 2'-O-Acetyl-5'-O-benzoyl-4-N-isobutyryl-3'-deoxycytidine 
• 143653-60-5 2'-O-acetyl-5'-O-benzoyl-3'-deoxy-5-methyluridine 

Relevant articles and documents

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