allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside
• CAS No.: 321896-01-9
• Molecular Formula: C₂₂H₃₄O₆Si
• Molecular Weight: 422.594
• Mol file: 321896-01-9.mol

Synonyms:allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Chemical Property of allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

There total 4 articles about allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-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: 98.0%

allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-α-D-glucopyranoside (321896-10-0) → allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside (321896-01-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1002/ejoc.200300580

Reference yield: 47.0%

tert-butyldimethylsilyl chloride (18162-48-6) + allyl 4,6-O-benzylidene-D-glucopyranoside (259882-15-0) → allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside (321896-01-9)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 60 ℃; for 16h;

DOI:10.1002/ejoc.201600071

Reference yield:

allyl 4,6-O-benzylidene-α-D-glucopyranoside (93382-48-0) → allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside (321896-01-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / pyridine / 0 °C

2: 99 percent / imidazole; DMAP / dimethylformamide

3: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

With pyridine; 1H-imidazole; dmap; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200300580

upstream raw materials:

allyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-α-D-glucopyranoside

allyl 4,6-O-benzylidene-α-D-glucopyranoside

allyl 4,6-O-benzylidene-2-O-pivaloyl-α-D-glucopyranoside

tert-butyldimethylsilyl chloride

Downstream raw materials:

allyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->2)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-α-D-glucopyranoside

allyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->2)-4,6-O-benzylidene-α-D-glucopyranoside

allyl 2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside

allyl 4-O-acetyl-2-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-α-D-glucopyranoside