pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside
• CAS No.: 161325-89-9
• Molecular Formula: C₅₈H₈₀O₁₅
• Molecular Weight: 1017.26
• Mol file: 161325-89-9.mol

Synonyms:pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Chemical Property of pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside

There total 3 articles about pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside 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: 70.0%

4-penten-1-yl-2,3,6-tri-O-benzyl-β-D-glucopyranoside + O-isopropenyl 2,3,4,6-tetra-O-pivaloyl-β-glucopyranoside (161325-87-7) → pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside (161325-89-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In acetonitrile; at 0 ℃;

DOI:10.1016/0040-4039(94)88449-8

Reference yield:

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide (81058-27-7) → pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside (161325-89-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / CHCl₃ / 27 h / Heating

2: 70 percent / 4 Angstroem MS, TMSOTf / acetonitrile / 0.08 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; In chloroform; acetonitrile;

DOI:10.1021/jo960190p

Reference yield:

pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside → pent-4-enyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-β-D-glucopyranoside (161325-89-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / sodium cyanoborohydride, HCl / tetrahydrofuran

2: 70 percent / 4 Angstroem MS, TMSOTf / acetonitrile / 0.08 h / 0 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; sodium cyanoborohydride; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo960190p

upstream raw materials:

O-isopropenyl 2,3,4,6-tetra-O-pivaloyl-β-glucopyranoside

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide