benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside
CAS No.:159353-28-3
Molecular Formula:C₃₂H₃₈O₈
Molecular Weight:550.649
Hs Code.:

Synonyms:benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside

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Technology Process of benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside

There total 8 articles about benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside 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: 72.6%

: 159353-25-0
benzyl 7-O-allyl-6-O-benzyl-2,3-O-isopropylidene-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside

: 159353-28-3
benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With toluene-4-sulfonic acid; In methanol; ethyl acetate; for 2h; Ambient temperature;
DOI:10.1016/0008-6215(94)84004-0

Reference yield:

: 77455-30-2
benzyl 6-O-triphenylmethyl-α-D-mannopyranoside

: 159353-28-3
benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 83.6 percent / toluene-p-sulfonic acid / 2 h / Ambient temperature

2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, THF, 2 h

3: 60.4 percent / 85percent formic acid / ethyl acetate / 1 h / Ambient temperature

4: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -60 °C

5: 1.262 g / tetrahydrofuran / 2 h / -30 °C

6: 1.) NaH / 1.) DMF, 0.5 h, 2.) DMF, RT, 4 h

7: 72.6 percent / toluene-p-sulfonic acid / ethyl acetate; methanol / 2 h / Ambient temperature

With formic acid; oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/0008-6215(94)84004-0

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 159353-28-3
benzyl 7-O-allyl-6-O-benzyl-4-O-p-methoxybenzyl-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, THF, 2 h

2: 60.4 percent / 85percent formic acid / ethyl acetate / 1 h / Ambient temperature

3: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -60 °C

4: 1.262 g / tetrahydrofuran / 2 h / -30 °C

5: 1.) NaH / 1.) DMF, 0.5 h, 2.) DMF, RT, 4 h

6: 72.6 percent / toluene-p-sulfonic acid / ethyl acetate; methanol / 2 h / Ambient temperature

With formic acid; oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/0008-6215(94)84004-0