(3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran

Base Information

• Chemical Name: (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran
• CAS No.: 194594-76-8
• Molecular Formula: C₃₇H₄₀O₆
• Molecular Weight: 580.721
• Mol file: 194594-76-8.mol

Synonyms:(3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran

Chemical Property of (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran

There total 12 articles about (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 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: 90.0%

C43H41NO7 + allyl alcohol (107-18-6) → (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran (194594-76-8)

Guidance literature:

With gold(III) chloride; 3F₆Sb^(1-)*3Ag⁽¹⁺⁾; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c5ob00248f

Reference yield: 86.0%

benzyl bromide (100-39-0) + α,β-O-allyl-D-mannopyranoside (182212-07-3,821794-45-0) → (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran (194594-76-8)

Guidance literature:

α,β-O-allyl-D-mannopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol102473k

Reference yield: 83.0%

benzyl bromide (100-39-0) + allyl α-D-mannopyranoside (41308-76-3,821794-45-0) → (3S,4S,5R,6R)-2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran (194594-76-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2010.04.014

upstream raw materials:

allyl α-D-mannopyranoside

benzyl chloride

tris(allyl)borate

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

allyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside

C₄₂H₄₂O₅

hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside