methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside

Base Information

• Chemical Name: methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside
• CAS No.: 219854-35-0
• Molecular Formula: C₂₂H₂₈O₈S
• Molecular Weight: 452.526
• Mol file: 219854-35-0.mol

Synonyms:methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside

Chemical Property of methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside

There total 2 articles about methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside 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: 95.0%

methanol (67-56-1) + 3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose (219854-34-9) → methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside (219854-35-0)

Guidance literature:

With hydrogenchloride; water;

DOI:10.1039/a806817h

Reference yield:

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (153186-10-8) → methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside (219854-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 0.33 h / 20 °C

2: 11.896 g / aq. HCl / 10 h

With pyridine; hydrogenchloride; 1: sulfonation / 2: Hydrolysis;

DOI:10.1021/jo000275x

Reference yield: 97.0%

acetic anhydride (108-24-7) + methyl 3,5-di-O-benzyl-4-C-methylsulfonyloxymethyl-α,β-D-ribofuranoside (219854-35-0) → Acetic acid (3R,4S,5S)-4-benzyloxy-5-benzyloxymethyl-5-methanesulfonyloxymethyl-2-methoxy-tetrahydro-furan-3-yl ester (219854-44-1)

Guidance literature:

With pyridine;

DOI:10.1039/a806817h

upstream raw materials:

methanol

3-O-benzyl-4-[(benzyloxy)methyl]-1,2-O-(1-methylethylidene)-5-O-(methylsulfonyl)-β-L-lyxofuranose

((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

Downstream raw materials:

Acetic acid (3R,4S,5S)-4-benzyloxy-5-benzyloxymethyl-5-methanesulfonyloxymethyl-2-methoxy-tetrahydro-furan-3-yl ester

methyl 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranoside

(1S,3RS,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-methoxy-2,5-dioxabicyclo[2.2.1]heptane

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane