methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside

Base Information

• Chemical Name: methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside
• CAS No.: 743422-33-5
• Molecular Formula: C₃₆H₄₈O₉
• Molecular Weight: 624.772
• Mol file: 743422-33-5.mol

Synonyms:methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside

Chemical Property of methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside

There total 1 articles about methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside 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: 89.0%

allyl bromide (106-95-6) + methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside (743422-31-3) → methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside (743422-33-5)

Guidance literature:

With sodium hydride; 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2004.04.020

Reference yield:

methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside (743422-33-5) → methyl 2,3-di-O-benzyl-5-deoxy-5-vinyl-β-D-ribo-L-threo-hepto-1,4-furanoside

Guidance literature:

Multi-step reaction with 4 steps

1: water; sulfuric acid / tetrahydrofuran / 20 h / Heating

2: sodium periodate / tetrahydrofuran; H₂O; diethyl ether / 0.5 h / 20 °C

3: 180 mg / sodium borohydride

4: 44 percent / water / Pd/C; p-toluenesulfonic acid / methanol / 2 h / 45 - 50 °C

With sodium tetrahydroborate; sodium periodate; sulfuric acid; water; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1016/j.tetasy.2004.04.020

upstream raw materials:

allyl bromide

methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside