3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose

Base Information

• Chemical Name: 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose
• CAS No.: 134877-43-3
• Molecular Formula: C20H18F2O8S
• Molecular Weight: 456.421
• Mol file: 134877-43-3.mol

Synonyms:3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose;

Chemical Property of 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose

Chemical Property:

• Refractive Index: 1.555
• Boiling Point: 588.4±50.0 °C(Predicted)
• PSA: 113.58000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 3.48620
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methyl-sulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonate β-D-erythro-Pentofuranose is an impurity of Gemcitabine (G305028), a potential anticancer agent.

Technology Process of 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose

There total 6 articles about 3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose 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: 100.0%

methanesulfonyl chloride (124-63-0) + (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate (1173824-58-2,143157-25-9,143157-22-6) → 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose (134877-42-2,134877-43-3,122111-11-9)

Guidance literature:

With triethylamine; In dichloromethane; at 23 ℃; for 2h;

DOI:10.1055/s-1992-26167

Reference yield: 97.8%

C19H16F2O6 (153012-08-9) + methanesulfonyl chloride (124-63-0) → 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose (134877-42-2,134877-43-3,122111-11-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

Reference yield:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8) → 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose (134877-42-2,134877-43-3,122111-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / LiAl(OBu-t)3H / diethyl ether; tetrahydrofuran / 1 h / 10 - 30 °C

2: 100 percent / triethylamine / CH₂Cl₂ / 2 h / 23 °C

With lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1055/s-1992-26167

upstream raw materials:

methanesulfonyl chloride

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate

ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate

Downstream raw materials:

C₂₇H₂₃F₂N₃O₇

3-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-ribofuranosyl)-7-acetyl-3,5,6,7-tetrahydro-2H-pyrrolo[2,3-d]pyrimidin-2-one

1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine

C₂₅H₂₅ClF₂N₃O₉P

Refernces

• 1、 -. "Purification method of gemcitabine intermediate". . . Retrieved 2021/06/22.
• 2、 -. "Industrial preparation process for key intermediate sulfonated saccharide of Gemcitabine". Paragraph 0043; 0044; 0045. . Retrieved 2017/08/28.