(2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

Base Information

• Chemical Name: (2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate
• CAS No.: 817204-32-3
• Molecular Formula: C31H26FN3O7
• Molecular Weight: 571.562
• European Community (EC) Number: 807-677-9
• DSSTox Substance ID: DTXSID901144030
• Nikkaji Number: J2.763.366H
• Mol file: 817204-32-3.mol

Synonyms:817204-32-3;(2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate;(2'R)-N-Benzoyl-2'-deoxy-2'-fluoro-2'-Methylcytidine 3',5'-dibenzoate;Cytidine, N-benzoyl-2'-deoxy-2'-fluoro-2'-methyl-, 3',5'-dibenzoate, (2'R)-;PSI-6130 derivative;Cytidine, N-benzoyl-2'-deoxy-2'-fluoro-2'-methyl-, 3',5'-dibenzoate,(2'R)-;(2'R)-N-benzoyl-2'-deoxy-2'-fluoro-2'-methyl-3',5'-dibenzoate Cytidine;[(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3-benzoyloxy-4-fluoro-4-methyloxolan-2-yl]methyl benzoate;Cytidine,N-benzoyl-2'-deoxy-2'-fluoro-2'-methyl-,3',5'-dibenzoate,(2'R)-;[(2R,3R,4R,5R)-5-(4-benzamido-2-oxo-1,2-dihydropyrimidin-1-yl)-3-(benzoyloxy)-4-fluoro-4-methyloxolan-2-yl]methyl benzoate;MFCD23106344;SCHEMBL12202843;DTXSID901144030;CS-M3033;N4,3',5'-tri-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methylcytidine;FD9071;AKOS025290708;AM85920;DS-7573;PB38796;AC-27671;A854796;2'Deoxy-2'fluoro-2'- methyl-N-(phenylcarbonyl) cytidine;(2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-ylbenzoate;(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(benzoyloxymethyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

Chemical Property of (2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

Chemical Property:

• Melting Point: 241 oC (dichloromethane/hexane)
• PKA: 8.51±0.20(Predicted)
• PSA: 125.82000
• Density: 1.34±0.1 g/cm3 (20 oC,760 mmHg)
• LogP: 4.27680
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 571.17547834
• Heavy Atom Count: 42
• Complexity: 1080

Purity/Quality:

≥98.0% ^*data from raw suppliers

2’-Defluro-2’-methyleneSofosbuvir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(OC1N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)COC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)F
• Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)COC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)F
• Uses: 2’-Defluro-2’-methylene Sofosbuvir is an impurity of Sofosbuvir (P839640).

Technology Process of (2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

There total 44 articles about (2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

C31H28FN3O7 → (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate (817204-32-3)

Guidance literature:

With manganese(IV) oxide; In toluene; at 20 ℃; for 2h;

Reference yield: 82.2%

C24H22FN3O6 + benzoyl chloride (98-88-4) → (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate (817204-32-3)

Guidance literature:

With pyridine; for 5h;

Reference yield: 72.5%

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate (1500076-79-8) + N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide (85743-99-3) → (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate (817204-32-3)

Guidance literature:

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; In chlorobenzene; at 23 ℃; for 0.25h;

With tin(IV) chloride; In chlorobenzene; at 50 - 60 ℃; for 18h;

upstream raw materials:

N⁴-benzoyl-1-(2-C-methyl-3,5-di-O-benzoyl-β-D-arabinofuranosyl)cytosine

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribofuranose

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

Downstream raw materials:

(2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

sofosbuvir

sofosbuvir

Refernces

• 1、 -. "Method for preparing sofosbuvir intermediate by using continuous flow micro-channel reactor". Paragraph 0033-0046. . Retrieved 2020/07/02.
• 2、 Liu, Tongchao,Tang, Jiadeng,Liang, Jianpeng,Chen, Yabin,Wang, Xiaowen,Shen, Jingkang,Zhao, Dongmei,Xiong, Bing,Cen, Jun-Da,Chen, Yue-Lei. "Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine". . p. 1203 - 1213. Retrieved 2019/01/29.