allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside

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Chemical Name:allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside
CAS No.:833489-23-9
Molecular Formula:C₄₇H₄₈O₉
Molecular Weight:756.893
Hs Code.:

Synonyms:allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside

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Chemical Property of allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside

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Technology Process of allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside

There total 3 articles about allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside 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: 50.0%

: 833489-22-8
allyl 2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-α-D-mannopyranoside

: 15014-25-2
malonic acid dibenzyl ester

: 833489-23-9
allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside

Guidance literature:: malonic acid dibenzyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

allyl 2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-α-D-mannopyranoside; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1021/ol0479444

Reference yield:

: 34212-64-1,641635-63-4
methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

: 833489-23-9
allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 50 percent / HCl / 6 h / 60 °C

2.1: 79 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 2 h / -40 °C

3.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 50 percent / tetrahydrofuran; hexane / -78 - 20 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methylpyridine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0479444

Reference yield:

: 93451-42-4
allyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside

: 833489-23-9
allyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 79 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 2 h / -40 °C

2.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 50 percent / tetrahydrofuran; hexane / -78 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0479444