3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene

Base Information

• Chemical Name: 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene
• CAS No.: 193546-84-8
• Molecular Formula: C₃₂H₃₆O₆
• Molecular Weight: 516.634
• Mol file: 193546-84-8.mol

Synonyms:3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene

Chemical Property of 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene

There total 5 articles about 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)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: 95.0%

acetic anhydride (108-24-7) + 3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene (161275-25-8) → 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene (193546-84-8)

Guidance literature:

DOI:10.1021/jo980996k

Reference yield: 76.0%

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside (55628-56-3,65827-55-6,68567-54-4,77790-45-5,77790-46-6,81969-44-0,99630-89-4,137567-77-2,125135-30-0) + allyl-trimethyl-silane (762-72-1) → 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene (193546-84-8) + acetic acid 2-allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (374900-65-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -40 - 20 ℃; for 8h;

DOI:10.1016/S0008-6215(01)00187-2

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene (193546-84-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethyldioxirane / CH₂Cl₂ / 0 °C

2: diethyl ether / -78 °C

3: pyridine

With pyridine; 3,3-dimethyldioxirane; In diethyl ether; dichloromethane;

DOI:10.1016/j.bmcl.2007.04.060

upstream raw materials:

acetic anhydride

3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

allyl-trimethyl-silane

Downstream raw materials:

(2R,3R,4S,4aS,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methyl-2,3,4,4a,8,8a-hexahydro-pyrano[3,2-b]pyran

(2S,3S,4S,5R,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-3-isopropenyloxy-tetrahydro-pyran

3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester