141846-57-3

Basic information

• Product Name: ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE)
• Synonyms: ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE);1-Chloro-3,5-di-O-toluoyl-2-deoxy-L-ribofuranose;1-Chloro-2-deoxy-3,5-di-O-toluoyl-L-ribose;2-Deoxy-3,5-di-O-p-toluoyl-α-L-ribofuranosyl Chloride;2-Deoxy-α-L-erythro-pentofuranosyl Chloride 3,5-Bis(4-methylbenzoate);Chloro-3,5-di-O-toluoyl-2-deoxy-α-L-ribofuranose;2-Deoxy-3,5-di-O-p-toluoyl-a-L-ribofuranosyl Chloride;2-Deoxy-a-L-erythro-pentofuranosyl Chloride 3,5-Bis(4-methylbenzoate)
• CAS NO: 141846-57-3
• Molecular Formula: C₂₁H₂₁ClO₅
• Molecular Weight: 388.845
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 141846-57-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 117-119°C
• Boiling Point: 518.414 °C at 760 mmHg
• Flash Point: 185.58 °C
• Appearance: White Solid
• Density: 1.283 g/cm³
• Refractive Index: 1.583
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly)
• Stability: Moisture Sensitive, Unstable in Solution
• CAS DataBase Reference: ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE)(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE)(141846-57-3)
• EPA Substance Registry System: ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE)(141846-57-3)

Safety Data

• Hazardous Substances Data: 141846-57-3(Hazardous Substances Data)

Usage

Description

ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE), also known as 2-Deoxy-3,5-di-O-p-toluoyl-α-L-ribofuranosyl Chloride (CAS# 141846-57-3), is a white solid compound that is useful in organic synthesis. It is a derivative of ribose, a sugar molecule, with specific modifications that make it valuable for various applications in the chemical and pharmaceutical industries.

Uses

Used in Organic Synthesis:
ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE) is used as a synthetic intermediate for the development of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex molecules, such as pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE) is used as a key component in the synthesis of novel drug candidates. Its chemical properties enable the development of new molecules with potential therapeutic applications, contributing to the advancement of drug discovery and innovation.
Used in Chemical Research:
ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE) is also used as a research tool in chemical laboratories. Its unique structure and reactivity make it an interesting subject for studying various chemical reactions and mechanisms, which can lead to a better understanding of organic chemistry and the development of new synthetic strategies.

InChI:InChI=1/C21H21ClO5/c1-13-3-7-15(8-4-13)20(23)25-12-18-17(11-19(22)26-18)27-21(24)16-9-5-14(2)6-10-16/h3-10,17-19H,11-12H2,1-2H3/t17?,18-,19+/m0/s1

Upstream product

• 4330-34-1 methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 874-60-2 4-methyl-benzoyl chloride 
• 364042-57-9 4-cyano-4-deoxy-1,2-O-isopropylidene-D-erythritol 
• 38996-14-4 (4R,5S)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 38996-09-7 5-bromo-2,5-dideoxy-D-threo-pentono-1,4-lactone 
• 82805-10-5 2,5-dibromo-2,5-dideoxy-D-lyxono-1,4-lactone 
• 15384-37-9 D-xylono-1,4-lactone 
• 87-72-9 D-Xylose 
• 817621-14-0 C₂₉H₂₈O₇ 
• 22837-36-1 methyl-2-deoxy-3,5-di-O-p-toluoyl-α-L-erythropentofuranoside 
• 210702-79-7 β ethyl 2-deoxy-L-ribofuranoside 
• 210702-78-6 α ethyl 2-deoxy-L-ribofuranoside 
• 817621-54-8 C₂₃H₂₆O₆ 

Downstream Products

• 16727-51-8 1-(2,6-bis-benzyloxy-pyridin-3-yl)-ξ-D-erythro-1,2-dideoxy-pentofuranose 
• 114184-61-1 4-(2-deoxy-3,5-di-O-p-tolyl-β-D-erythro-pentofuranosyl)-5-methyl-1,4-thiazine-3-one 
• 4330-24-9 (furan-2-yl)methyl 4-methylbenzoate 
• 79378-88-4 4-Amino-8-<2-desoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-rinofuranosyl>-7(8H)-pteridinon 
• 79378-90-8 4-<2-Desoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-ribofuranosylamino>-7(8H)-pteridinon 
• 79395-76-9 4-Amino-8-<2-desoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-ribofuranosyl>-2-phenyl-7(8H)-pteridinon 
• 50256-07-0 1-[O³,O⁵-bis-(4-methyl-benzoyl)-β-D-erythro-2-deoxy-pentofuranosyl]-6,7-dimethyl-1H-pteridine-2,4-dione 
• 132163-37-2 5-benzyl-2'-deoxy-3',5'-bis(O-p-toluoyl)uridine 
• 132163-38-3 5-benzyl-1-(2-deoxy-3,5-bis(O-p-toluoyl)-α-D-ribofuranosyl)uracil 
• 156270-76-7 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-azauracyl 
• 91713-27-8 methyl 5-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazole-4-carboxylate 
• 91713-25-6 methyl 4-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazole-5-carboxylate 
• 91713-24-5 methyl 4-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)imidazole-5-carboxylate 
• 91713-26-7 methyl 5-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)imidazole-4-carboxylate 

Relevant articles and documents

Convenient preparation of 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

By using acetyl chloride as HCl generator, the procedure for the Hoffer preparation of the α-chloro sugar 4a was significantly improved. The α-configuration of the chloro atom was confirmed by using NOE measurement. Sequential transformation of 4a to the β-anomer and to the furfuryl derivative 6 was studied.

Benzimidazole derivative BI305 and preparation method and application thereof

The invention discloses a benzimidazole derivative BI305 and a preparation method thereof, and the chemical name of the benzimidazole derivative BI305 is 1-[tetrahydro-4-hydroxy-5-(hydroxymethyl) furan-2-yl]-N, N-dimethyl-1H-benzo [d] imidazole-4-formamide. The benzimidazole derivative and the pharmaceutically acceptable salt, solvate and hydrate thereof have excellent anti-tumor in-vivo and in-vitro activity on MCF-7, SK-BR-3, HCT 116, U-118 MG, U-87 MG and MDA-MB-468, and have a good application prospect in preparation of anti-tumor drugs.

Synthesis of beta-L-2'-deoxy nucleosides

An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.