methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside

Base Information

• Chemical Name: methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside
• CAS No.: 221552-92-7
• Molecular Formula: C₂₀H₁₉FO₅S
• Molecular Weight: 390.432
• Mol file: 221552-92-7.mol

Synonyms:methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside

Chemical Property of methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside

There total 3 articles about methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside 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: 58.0%

benzoyl chloride (98-88-4) + (2R,3S,4S)-4-Fluoro-2-hydroxymethyl-5-methoxy-tetrahydro-thiophen-3-ol → methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside (221552-92-7)

Guidance literature:

DOI:10.1080/15257779908041569

Reference yield:

3-deoxy-3-fluoro-5-S-acetyl-6-O-acetyl-5-thio-α-D-glucofuranose → methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside (221552-92-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaIO₄

1.2: HCl

2.1: 58 percent

With sodium periodate; 1.1: Oxidation / 1.2: Etherification / 2.1: Esterification;

DOI:10.1080/15257779908041569

Reference yield:

benzoyl chloride (98-88-4) + 3-deoxy-5,6-di-O,S-acetyl-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose (197647-11-3) → methyl 2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranoside (221552-92-7)

Guidance literature:

3-deoxy-5,6-di-O,S-acetyl-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose; With trifluoroacetic acid;

With sodium periodate; In methanol; water;

benzoyl chloride; Further stages;

upstream raw materials:

benzoyl chloride

3-deoxy-5,6-di-O,S-acetyl-3-fluoro-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose

Downstream raw materials:

1-O-acetyl-2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranose

9-(2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranosyl)-2,6-diaminopurine

((2R,3S,4S)-3-(benzoyloxy)-5-bromo-4-fluorothiolan-2-yl)methyl benzoate

4-acetyl-1-(2-deoxy-3,5-di-O-benzoyl-2-fluoro-4-thio-α,β-D-arabino-pentofuranosyl)cytosine