(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

Base Information

Chemical Name:(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
CAS No.:1428421-65-1
Molecular Formula:C₆₇H₉₃N₃O₉Si
Molecular Weight:1112.58
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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:

: (2S,3S,4R,5S)-2-azido-3,4,5-tris(benzyloxy)octadecan-1-ol

: trichloroacetimidoyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-d-galactopyranoside

: 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

Guidance literature:: (2S,3S,4R,5S)-2-azido-3,4,5-tris(benzyloxy)octadecan-1-ol; trichloroacetimidoyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-d-galactopyranoside; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve;

With silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 17h; Molecular sieve;
DOI:10.1016/j.carres.2013.01.010

Reference yield:

: (2S,3S,4R,5S)-2-azido-1-(tert-butyldimethylsilyl)oxy-3,4,5-tris(benzyloxy)octadecane

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

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

2.2: 17 h / 0 - 20 °C / Molecular sieve

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

Reference yield:

: 61277-56-3
1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranose

: 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

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium hydroxide / methanol / 1 h / 20 °C

2.1: 1H-imidazole / dichloromethane / 1.5 h / 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -10 °C / Inert atmosphere

3.2: 16.25 h / -10 - 20 °C

4.1: palladium 10% on activated carbon; hydrogen / hexane / 0.83 h / 20 °C

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

5.2: 3.5 h / 0 - 20 °C

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

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

7.2: 17 h / 0 - 20 °C / Molecular sieve

With 1H-imidazole; n-butyllithium; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; triphenylphosphine; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 3.1: |Wittig Olefination / 3.2: |Wittig Olefination;
DOI:10.1016/j.carres.2013.01.010