2'-Deoxy-2',2'-difluoro ThyMidine

Base Information

• Chemical Name: 2'-Deoxy-2',2'-difluoro ThyMidine
• CAS No.: 95058-80-3
• Molecular Formula: C10H12F2N2O5
• Molecular Weight: 278.20900
• Mol file: 95058-80-3.mol

Synonyms:2'-Deoxy-2',2'-difluoro Thymidine;2'-DEOXY-2',2'-DIFLUOROTHYMIDINE;

Chemical Property of 2'-Deoxy-2',2'-difluoro ThyMidine

Chemical Property:

• PSA: 104.55000
• LogP: -1.26910

Purity/Quality:

97% ^*data from raw suppliers

2’-Deoxy-2’,2’-difluoroThymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Gemcitabine (G305000) intermediate.

Technology Process of 2'-Deoxy-2',2'-difluoro ThyMidine

There total 5 articles about 2'-Deoxy-2',2'-difluoro ThyMidine 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: 86.0%

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine (908337-67-7) → 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine (95058-80-3)

Guidance literature:

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine; With sodium methylate; In methanol; at 20 ℃; Inert atmosphere;

In methanol;

DOI:10.1016/j.bmc.2011.05.037

Reference yield:

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate (1173824-58-2,143157-25-9,143157-22-6) → 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine (95058-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere

2.2: 20 °C

3.1: sodium methylate / methanol / 20 °C / Inert atmosphere

3.2: Amberlite

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; triethylamine; In methanol; 1,1-dichloroethane; dichloromethane;

DOI:10.1016/j.bmc.2011.05.037

Reference yield:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8) → 1-(2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine (95058-80-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / 1,1-dichloroethane / 10 h / 90 - 100 °C / Inert atmosphere

3.2: 20 °C

4.1: sodium methylate / methanol / 20 °C / Inert atmosphere

4.2: Amberlite

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; 1,1-dichloroethane; dichloromethane;

DOI:10.1016/j.bmc.2011.05.037

upstream raw materials:

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine

(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

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose