(2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

Base Information

Chemical Name:(2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside
CAS No.:1428421-66-2
Molecular Formula:C₆₇H₉₅NO₉Si
Molecular Weight:1086.58
Hs Code.:

Synonyms:(2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

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Chemical Property of (2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

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Technology Process of (2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

There total 13 articles about (2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside 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: 77.0%

: 1428421-65-1
(2S,3S,4R,5S)-2-azido-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

: 1428421-66-2
(2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

Guidance literature:: (2S,3S,4R,5S)-2-azido-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside; With trimethylphosphane; In tetrahydrofuran; at 20 ℃; for 2h;

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h;
DOI:10.1016/j.carres.2013.01.010

Reference yield:

: 1428421-61-7
(2R,3S,4R,5S)-3,4,5-tris(benzyloxy)-1-[(tert-butyldimethylsilyl)oxy]octadecan-2-ol

: 1428421-66-2
(2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0.17 h / 20 °C / Inert atmosphere

1.2: 3.5 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

3.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve

3.2: 17 h / 0 - 20 °C / Molecular sieve

4.1: trimethylphosphane / tetrahydrofuran / 2 h / 20 °C

4.2: 2 h / 20 °C

With tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; trimethylphosphane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.carres.2013.01.010

Reference yield:

: 1242144-05-3
4-methylphenyl 4,6-O-di-tert-butylsilylidene-1-thio-β-D-galactopyranoside

: 1428421-66-2
(2S,3S,4R,5S)-2-amino-3,4,5-tris(benzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / acetone / 0.67 h / -20 °C

3.1: caesium carbonate / dichloromethane / 16 h / 20 °C

4.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve

4.2: 17 h / 0 - 20 °C / Molecular sieve

5.1: trimethylphosphane / tetrahydrofuran / 2 h / 20 °C

5.2: 2 h / 20 °C

With N-Bromosuccinimide; sodium hydride; caesium carbonate; trimethylphosphane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; mineral oil;
DOI:10.1016/j.carres.2013.01.010