2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone

Base Information

• Chemical Name: 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone
• CAS No.: 95058-77-8
• Molecular Formula: C5H6F2O4
• Molecular Weight: 168.097
• Mol file: 95058-77-8.mol

Synonyms:(4S,5S)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

Chemical Property of 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone

Chemical Property:

• Melting Point: 271-273 °C (decomp)
• Boiling Point: 348.5±42.0 °C(Predicted)
• PKA: 10.24±0.60(Predicted)
• PSA: 66.76000
• Density: 1.62±0.1 g/cm3(Predicted)
• LogP: -1.09970

Purity/Quality:

99% ^*data from raw suppliers

2-DEOXY-2,2-DIFLUORO-D-ERYTHRO-PENTONIC ACID GAMMA-LACTONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone

There total 20 articles about 2-Deoxy-2,2-difluoro -D-threo-pentonic acid γ-lactone 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: 99.9%

D-erythro-3-(hydroxy)-2,2-difluoro-3-(2,2-dimethyldioxolan-4-yl)propionic acid dicyclohexylammonium salt + trifluoroacetic acid (76-05-1) → 2-deoxy-2,2-difluoro-1-carbonylribose (95058-77-8) + dicyclohexylammonium trifloroacetate

Guidance literature:

With water; In acetonitrile; at 78 ℃; for 3 - 10h; Product distribution / selectivity; Heating / reflux;

Reference yield: 95.0%

(erytro) ethyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxy propionate (95058-92-7,166376-97-2) → 2-deoxy-2,2-difluoro-1-carbonylribose (95058-77-8)

Guidance literature:

With Dowex 50WX₈-100; In methanol; water; at 20 - 25 ℃; for 48h;

Reference yield: 94.0%

ethyl 2,2-difluoro-3(R)-hydroxy-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propionate (95058-92-7,166376-97-2) → 2-deoxy-2,2-difluoro-1-carbonylribose (95058-77-8)

Guidance literature:

With Dowex 50W-X₁₂ resin; In methanol; water; for 96h; Ambient temperature;

DOI:10.1021/jo00246a002

upstream raw materials:

3-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-2,2-difluoro-3-triethylsilanyloxy-propionic acid ethyl ester

ethyl 2,2-difluoro-3(R)-hydroxy-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propionate

(erytro) ethyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxy propionate

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

Downstream raw materials:

3,5-bis(tert-butyl-diphenylsilyloxy)-2-deoxy-2,2-difluoro-1-oxoribose

pyridine hydrochloride

(3R,4R)-5-trityloxy-3-hydroxy-2,2-difluoro-pentanoic acid γ-lactone

(2R,3R)-4,4-difluoro-5-(methylsulfonyloxy)-2-(trityloxymethyl)tetrahydrofuran-3-yl benzoate

Refernces

• 1、 -. "High-selectivity synthesis method for gemcitabine intermediate". Paragraph 0055-0056. . Retrieved 2021/01/29.
• 2、 -. "Method for preparing Gemcitabine intermediate from chiral catalyst". Paragraph 0031; 0036; 0037; 0042; 0043; 0048. . Retrieved 2019/05/28.