(2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane

Base Information

Chemical Name:(2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane
CAS No.:918334-17-5
Molecular Formula:C₅₁H₇₁NO₈Si
Molecular Weight:854.212
Hs Code.:

Synonyms:(2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane

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Chemical Property of (2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane

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Technology Process of (2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane

There total 11 articles about (2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane 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: 96.0%

: (2S,3S,4R)-2-azido-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)non-6-ene

: 918334-17-5
(2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 12h;
DOI:10.1016/j.carres.2006.09.006

Reference yield:

: 918334-08-4
allyl 4,6-O-di-tert-butylsilylene-α-D-galactopyranoside

: 918334-17-5
(2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 66 percent / sodium hydride / dimethylformamide / 15 h / -20 - 20 °C

2.1: hydrogen / [(1,5-cyclooctadiene)bis(methyldiphenylphosphine)Ir(I)]PF₆ / tetrahydrofuran / 1.17 h / 20 °C

2.2: 52 percent / acetyl chloride / methanol; CH₂Cl₂ / 1.5 h

3.1: DBU / CH₂Cl₂ / 1 h / 0 °C

4.1: 66 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -40 - 0 °C

5.1: 96 percent / hydrogen / Pd/C / methanol / 12 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2006.09.006

Reference yield:

: (2S,3S,4R)-2-azido-3,4-bis(benzyloxy)non-6-en-1-ol

: 918334-17-5
(2S,3S,4R)-2-amino-3,4-bis(benzyloxy)-1-(2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyloxy)nonane

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -40 - 0 °C

2: 96 percent / hydrogen / Pd/C / methanol / 12 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1016/j.carres.2006.09.006