2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose

Base Information

• Chemical Name: 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose
• CAS No.: 1015447-26-3
• Molecular Formula: C28H24O8S
• Molecular Weight: 520.55036
• Mol file: 1015447-26-3.mol

Synonyms:1-O-ACETYL-2,3,5-TRI-O-BENZOYL-4-THIO-D-RIBOFURANOSE;

Chemical Property of 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose

Chemical Property:

• PSA: 130.50000
• LogP: 4.29920

Purity/Quality:

99%, ^*data from raw suppliers

(3R,4S,5R)-2-Acetoxy-5-((benzoyloxy)methyl)tetrahydrothiophene-3,4-diyldibenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose

There total 7 articles about 2,3,5-Tri-O-benzoyl-1-O-acetyl-4-thio-D-ribofuranose 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: 70.0%

methyl 2,3,5-tri-O-benzoyl-α,β-4-thio-D-ribofuranoside (1015447-25-2) + acetic anhydride (108-24-7) → 2,3,5-tri-O-benzoyl-1-O-acetyl-β-4-thio-D-ribofuranose (1015447-26-3) + 2,3,5-tri-O-benzoyl-1-O-acetyl-α-4-thio-D-ribofuranose

Guidance literature:

With sulfuric acid; In acetic acid; at 20 ℃; for 1h;

DOI:10.1021/jo7026596

Reference yield:

2,3,5-tri-O-benzoyl-4-thio-D-ribofuranose + acetic anhydride (108-24-7) → 2,3,5-tri-O-benzoyl-1-O-acetyl-β-4-thio-D-ribofuranose (1015447-26-3)

Guidance literature:

With dmap; In ethyl acetate; at 20 ℃; for 73h;

Reference yield:

2,3,5-Tri-O-benzoyl-D-ribofuranose (115459-50-2) → 2,3,5-tri-O-benzoyl-1-O-acetyl-β-4-thio-D-ribofuranose (1015447-26-3)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine; methanol / 17.92 h / 0 - 20 °C

2: 1-methyl-1H-imidazole / acetonitrile / 18 h / 20 °C

3: lithium bromide / butanone / 18 h / 80 °C

4: Glyoxilic acid / acetonitrile / 18 h / 70 °C

5: sodium hydrogen sulfide monohydrate; water / N,N-dimethyl-formamide / 0.5 h / 0 °C

6: pyridine / 0.5 h / 20 °C

With pyridine; 1-methyl-1H-imidazole; methanol; sodium hydrogen sulfide monohydrate; water; triethylamine; Glyoxilic acid; lithium bromide; In N,N-dimethyl-formamide; acetonitrile; butanone;

DOI:10.1039/d1ob02097h

upstream raw materials:

methyl 2,3,5-tri-O-benzoyl-α,β-4-thio-D-ribofuranoside

acetic anhydride

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2,3,5-Tri-O-benzoyl-D-ribofuranose

Refernces

• 1、 -. "SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-?-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME". Paragraph 1626-1628; 1724-1726. . Retrieved 2015/06/10.