methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside
• CAS No.: 365418-33-3
• Molecular Formula: C₂₄H₂₆O₆
• Molecular Weight: 410.467
• Mol file: 365418-33-3.mol

Synonyms:methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside

Chemical Property of methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside

There total 2 articles about methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-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: 62.0%

allyltributylstanane (24850-33-7) + Benzoic acid (2R,4aR,6S,7R,8S,8aR)-6-methoxy-8-phenoxythiocarbonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (365418-32-2) → methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside (365418-33-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In toluene; for 4h; Heating;

DOI:10.1021/jo030039x

Reference yield:

methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside (28642-64-0,35823-97-3,38992-99-3,51591-23-2,55169-75-0,56253-26-0,72659-78-0,80041-30-1,80299-59-8,86420-70-4,86420-72-6,91685-06-2,99265-94-8,109010-33-5,118246-05-2,126255-07-0) → methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside (365418-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / NHS; pyridine / toluene / 1 h / 20 °C

2: 62 percent / AIBN / toluene / 4 h / Heating

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; 2,2'-azobis(isobutyronitrile); In toluene;

DOI:10.1021/jo030039x

Reference yield: 94.0%

benzyl bromide (100-39-0) + methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside (365418-33-3) → methyl 2-O-benzyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside (365418-34-4)

Guidance literature:

methyl 2-O-benzoyl-4,6-di-O-benzylidene-3-allyl-3-deoxy-α-D-glucopyranoside; With sodium hydride; In methanol; at 20 ℃; for 2h;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; at 23 ℃; for 12h;

DOI:10.1021/jo030039x

upstream raw materials:

allyltributylstanane

Benzoic acid (2R,4aR,6S,7R,8S,8aR)-6-methoxy-8-phenoxythiocarbonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

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

methyl (R)-4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-glucopyranoside

methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-(2-ethanoic acid)-α-D-glucopyranoside

((2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl)-acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester