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

Base Information

• Chemical Name: benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS No.: 142698-31-5
• Molecular Formula: C₃₄H₃₄O₆
• Molecular Weight: 538.64
• Mol file: 142698-31-5.mol

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

Chemical Property of benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

There total 11 articles about benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-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: 94.0%

benzyl bromide (100-39-0) + benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside (79549-73-8) → benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (142698-31-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 7h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b04279

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (142698-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / Inert atmosphere

2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3: sodium hydride / N,N-dimethyl-formamide / 7 h / 0 - 20 °C / Inert atmosphere

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.9b04279

Reference yield:

D-Glucose (2280-44-6) → benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (142698-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / Inert atmosphere

2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3: sodium hydride / N,N-dimethyl-formamide / 7 h / 0 - 20 °C / Inert atmosphere

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.9b04279

upstream raw materials:

D-Galactose

(4aR,7R,8R,8aR)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol

benzyl bromide

benzaldehyde dimethyl acetal

Downstream raw materials:

Benzyl 2,3-di-O-benzyl-α-D-glucopyranoside

benzyl 2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside