3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene

Base Information

• Chemical Name: 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene
• CAS No.: 1072523-01-3
• Molecular Formula: C₃₀H₃₂O₅
• Molecular Weight: 472.581
• Mol file: 1072523-01-3.mol

Synonyms:3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene

Chemical Property of 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene

There total 8 articles about 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene 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: 81.0%

2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranosyl picolinate + allyl-trimethyl-silane (762-72-1) → 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene (1072523-01-3)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; stereoselective reaction; Molecular sieve; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c01041

Reference yield: 71.0%

allyltributylstanane (24850-33-7) + phenylsulfenyl 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene)-β-D-glucopyranoside (219586-38-6) → 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene (1072523-01-3)

Guidance literature:

phenylsulfenyl 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene)-β-D-glucopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 ℃; Inert atmosphere;

allyltributylstanane; In dichloromethane; at -78 - 20 ℃; optical yield given as %de;

DOI:10.1021/ol801710s

Reference yield: 58.0%

allyltributylstanane (24850-33-7) + S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (87470-70-0) → 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene-α-D-glucopyranosyl)-1-propene (1072523-01-3)

Guidance literature:

S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -65 ℃; for 0.75h; Molecular sieve;

allyltributylstanane; In dichloromethane; at -65 ℃; Molecular sieve;

DOI:10.1021/jo3011655

upstream raw materials:

trifluoromethanesulfonyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

allyltributylstanane

allyl-trimethyl-silane

phenylsulfenyl 3-(2',3'-di-O-benzyl-4',6'-O-benzylidene)-β-D-glucopyranoside