methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside

Base Information

Chemical Name:methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside
CAS No.:1330004-38-0
Molecular Formula:C₄₇H₆₂O₁₁Si
Molecular Weight:831.088
Hs Code.:

Synonyms:methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside

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Technology Process of methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside

There total 3 articles about methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-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: 71.0%

: 25320-59-6
tetra-O-benzyl glucopyranosyl chloride

: 74247-81-7
6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside

: 1330004-38-0
methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside

Guidance literature:: With diphenylborate ethanolamine ester; silver(l) oxide; In acetonitrile; at 23 ℃; for 16h; regioselective reaction; Inert atmosphere;
DOI:10.1021/ja2062715

Reference yield:

: 74247-81-7
6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside

: 213202-73-4
2,3,4,6-tetra-O-benzyl-1-O-methanesulfonyl-D-glucopyranoside

: 1330004-38-0
methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside

: methyl 6-O-tert-butyldimethylsilyl-3-O-(2',3',4',6'-tetra-O-benzyl-D-glucopyranosyl)-α-D-mannopyranoside

Guidance literature:: In dichloromethane; at 23 ℃; stereoselective reaction;
DOI:10.1021/jacs.6b06943

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 1330004-38-0
methyl 6-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 1,3,5-trichloro-2,4,6-triazine; potassium carbonate / dichloromethane; N,N-dimethyl-formamide / 4 h / 23 - 45 °C / Inert atmosphere

2: diphenylborate ethanolamine ester; silver(l) oxide / acetonitrile / 16 h / 23 °C / Inert atmosphere

With 1,3,5-trichloro-2,4,6-triazine; diphenylborate ethanolamine ester; potassium carbonate; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2: Koenigs-Knorr synthesis;
DOI:10.1021/ja2062715