((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methylsulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methylsulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 134877-42-2
• Molecular Formula: C20H18F2O8S
• Molecular Weight: 456.421
• European Community (EC) Number: 603-878-9
• DSSTox Substance ID: DTXSID301129773
• Mol file: 134877-42-2.mol

Synonyms:((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methylsulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzoate;134877-42-2;134877-43-3;[(2R,3R,5R)-3-benzoyloxy-4,4-difluoro-5-methylsulfonyloxyoxolan-2-yl]methyl benzoate;((2R3R5R)-3-(Benzoyloxy)-44-difluoro-5-((methylsulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzoate;((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methyl-sulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzoate;3,5-bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose;C20H18F2O8S;2-Deoxy-2,2-difluoro-3,5-O-dibenzoylribose mesylate;SCHEMBL8713071;LIAQHZDWFACWFK-GPMSIDNRSA-N;DTXSID301129773;MFCD22422479;AKOS015896201;DS-16124;CS-0357062;D84356;3,5-Bis(benzoyl)-1-methanesulfonyloxy-2-deoxy-2,2-difluororibose(beta-form);alpha-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate 1-methanesulfonate;((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methylsulfonyl)oxy)tetrahydrofuran-2-yl)methylbenzoate;[(2R,3R,5R)-3-(BENZOYLOXY)-4,4-DIFLUORO-5-(METHANESULFONYLOXY)OXOLAN-2-YL]METHYL BENZOATE

Chemical Property of ((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methylsulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

• Refractive Index: 1.583
• 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
• 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:

2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonateα-D-erythro-Pentofuranose ^*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)O[C@@H]1C([C@@H]([C@H](O1)COC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)(F)F
• Uses: 2-Deoxy-2,2-difluoro-3,5-dibenzoate-1-methanesulfonate α-D-erythro-Pentofuranose is an impurity of Gemcitabine (G305028), a potential anticancer agent.

Technology Process of ((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methylsulfonyl)oxy)tetrahydrofuran-2-yl)methyl benzoate

There total 8 articles about ((2R,3R,5R)-3-(Benzoyloxy)-4,4-difluoro-5-((methylsulfonyl)oxy)tetrahydrofuran-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: 91.0%

methanesulfonyl chloride (124-63-0) + 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-α-ribofuranose (143157-25-9,143157-22-6) → 2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate (134877-42-2)

Guidance literature:

at 0 - 30 ℃; for 2.5h;

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:

2’-deoxy-2’,2’-difluoro-cytidine

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

gemcitabine hydrochloride

4-chloro-7-[3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

Refernces

• 1、 -. "Purification method of gemcitabine intermediate". . . Retrieved 2021/06/22.
• 2、 -. "Preparation method of gemcitabine intermediate methylsulfonyl ester". Paragraph 0022; 0026-0027; 0028-0029; 0030-0031; 0032-0041. . Retrieved 2019/04/30.