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

Base Information

Chemical Name:methyl 6-deoxy-6-[bis(benzyloxycarbonyl)methyl]-2,3,4-tri-O-benzyl-α-D-mannopyranoside
CAS No.:833489-18-2
Molecular Formula:C₄₅H₄₆O₉
Molecular Weight:730.855
Hs Code.:

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

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

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

There total 2 articles about methyl 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: 54.0%

: 15014-25-2
malonic acid dibenzyl ester

: 221545-35-3
((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate

: 833489-18-2
methyl 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;

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

Reference yield:

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

: 833489-18-2
methyl 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: 85 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1.5 h / -40 °C

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

2.2: 54 percent / tetrahydrofuran; hexane / 6 h / -78 - 20 °C

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