[(2S,3S)-3-benzoyloxy-4,4-difluoro-5-methylsulfonyloxyoxolan-2-yl]methyl benzoate

Base Information

• Chemical Name: [(2S,3S)-3-benzoyloxy-4,4-difluoro-5-methylsulfonyloxyoxolan-2-yl]methyl benzoate
• CAS No.: 122111-11-9
• Molecular Formula: C₂₀H₁₈F₂O₈S
• Molecular Weight: 456.421
• Hs Code.: 2932190090
• European Community (EC) Number: 685-280-8
• Mol file: 122111-11-9.mol

Synonyms:2-deoxy-2,2-difluoro-d-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate;122111-11-9

Chemical Property of [(2S,3S)-3-benzoyloxy-4,4-difluoro-5-methylsulfonyloxyoxolan-2-yl]methyl benzoate

Chemical Property:

• Appearance/Colour: Brown liquid
• Vapor Pressure: 2.41E-11mmHg at 25°C
• Refractive Index: 1.652
• Boiling Point: 588.439 °C at 760 mmHg
• Flash Point: 309.677 °C
• PSA: 113.58000
• Density: 1.464 g/cm³
• LogP: 3.48620
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 456.06904503
• Heavy Atom Count: 31
• Complexity: 739

Purity/Quality:

99% ^*data from raw suppliers

2-Deoxy-2,2-difluoro-D-erythro-ribofuranose-3,5-dibenzoate 1-Methanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)OC1C(C(C(O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)(F)F
• Isomeric SMILES: CS(=O)(=O)OC1C([C@H]([C@@H](O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)(F)F
• Uses: Gemcitabine intermediate Gemcitabine intermediate.

Technology Process of [(2S,3S)-3-benzoyloxy-4,4-difluoro-5-methylsulfonyloxyoxolan-2-yl]methyl benzoate

There total 5 articles about [(2S,3S)-3-benzoyloxy-4,4-difluoro-5-methylsulfonyloxyoxolan-2-yl]methyl 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: 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:

3',5'-di-O-benzoyl-2'deoxy-2',2',5-trifluorocytidine

2'-deoxy-2',2'-difluorocytidine hydrochloride

gemcitabine hydrochloride

C₂₅H₂₅F₂IN₃O₉P

Refernces

• 1、 -. "Purification method of gemcitabine intermediate". . . Retrieved 2021/06/22.
• 2、 -. "SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF". Paragraph 0866; 0867. . Retrieved 2013/07/05.