Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside

Base Information

• Chemical Name: Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside
• CAS No.: 119943-96-3
• Molecular Formula: C₂₁H₂₄O₅
• Molecular Weight: 356.419
• Mol file: 119943-96-3.mol

Synonyms:Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside

Chemical Property of Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside

There total 17 articles about Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside 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: 94.0%

Methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(phenoxythiocarbonyl)-α-D-glucopyranoside (145149-82-2) → Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside (119943-96-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 1.5h;

DOI:10.1016/S0008-6215(00)90923-6

Reference yield: 90.0%

benzyl bromide (100-39-0) + methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (6752-48-3,16718-95-9,18424-62-9,19877-02-2,22886-97-1,52153-29-4,52612-68-7,55331-65-2,64978-95-6,65725-24-8,66512-93-4,67968-51-8,72904-80-4,77481-69-7,131615-73-1,138663-49-7,151214-39-0) → Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside (119943-96-3)

Guidance literature:

In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00005-2

Reference yield: 68.0%

methanol (67-56-1) + p-methylphenyl 3-O-benzyl-4,6-O-benzylidine-2-deoxy-1-thio-D-glucopyranoside → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (1423498-07-0) + Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside (119943-96-3)

Guidance literature:

p-methylphenyl 3-O-benzyl-4,6-O-benzylidine-2-deoxy-1-thio-D-glucopyranoside; With silver trifluoromethanesulfonate; p-toluenesulfonyl chloride; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere; Molecular sieve;

methanol; In dichloromethane; at -78 ℃; Overall yield = 76 %; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201203418

upstream raw materials:

Methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(phenoxythiocarbonyl)-α-D-glucopyranoside

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

benzyl bromide

methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

C₇₅H₁₀₂O₁₃Si

C₇₅H₁₀₀O₁₂Si

C₇₁H₉₀O₁₂S

{(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-2-[(2R,4aR,6S,7R,9S,10aS)-7-(4-methoxy-benzyloxy)-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-6-ylmethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane