tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside
CAS No.:189454-46-4
Molecular Formula:C₂₂H₃₅NO₆Si
Molecular Weight:437.608
Hs Code.:

Synonyms:tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside

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Chemical Property of tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside

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Technology Process of tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside

There total 6 articles about tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside 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: 72.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 189454-45-3
tert-butyldimethylsilyl 3-amino-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside

: 189454-46-4
tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside

Guidance literature:: With triethylamine; In dichloromethane; for 3h;
DOI:10.1021/jm9800752

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 189454-46-4
tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 43 percent / imidazole / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 18 h

2: 97 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

3: 85 percent / p-TsOH / acetonitrile / 1 h / Ambient temperature

4: 98 percent / H₂, Et₃N / 10 percent Pd/C / ethyl acetate / 760 Torr

5: 72 percent / Et₃N / CH₂Cl₂ / 3 h

With 1H-imidazole; hydrogen; sodium methylate; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jm9800752

Reference yield:

: 4,6-di-O-acetyl-3-azido-2,3-dideoxy-D-erythro-hexopyranose

: 189454-46-4
tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 43 percent / imidazole / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 18 h

2: 97 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

3: 85 percent / p-TsOH / acetonitrile / 1 h / Ambient temperature

4: 98 percent / H₂, Et₃N / 10 percent Pd/C / ethyl acetate / 760 Torr

5: 72 percent / Et₃N / CH₂Cl₂ / 3 h

With 1H-imidazole; hydrogen; sodium methylate; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jm9800752