(2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene

Base Information

Chemical Name:(2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene
CAS No.:877380-45-5
Molecular Formula:C₆₆H₈₁N₃O₈
Molecular Weight:1044.38
Hs Code.:

Synonyms:(2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene

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Chemical Property of (2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene

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Technology Process of (2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene

There total 5 articles about (2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene 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: 55.0%

: 6386-24-9
2,3,4,6-tetra-O-benzyl-D-galactopyranose

: 471891-18-6
(2S,3S,4R,5Z)-2-azido-3,4-dibenzyloxy-5-octadecen-1-ol

: (2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene

: 877380-45-5
(2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene

Guidance literature:: 2,3,4,6-tetra-O-benzyl-D-galactopyranose; With 2,6-di-tert-butyl-4-methylpyridine; dimethylsulfide; trifluoromethylsulfonic anhydride; In dichloromethane; at -45 - 20 ℃; for 1.5h;

(2S,3S,4R,5Z)-2-azido-3,4-dibenzyloxy-5-octadecen-1-ol; In dichloromethane; at 20 ℃; for 10h;
DOI:10.1021/jo051518u

Reference yield:

: 13266-02-9
n-tridecyltriphenylphosphonium bromide

: 877380-45-5
(2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 87 percent / potassium hexamethyldisilylamide / tetrahydrofuran; toluene / 3 h / -84 °C

2.1: 2,6-tert-butyl-4-methylpyridine; trifluoromethanesufonic anhydride; dimethyl sulfide / CH₂Cl₂ / 1.5 h / -45 - 20 °C

2.2: 55 percent / CH₂Cl₂ / 10 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; dimethylsulfide; trifluoromethylsulfonic anhydride; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo051518u

Reference yield:

: 4-azido-2,3-di-O-benzyl-4-deoxy-L-ribopyranose

: 877380-45-5
(2S,3S,4R,5Z)-2-azido-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-3,4-dibenzyloxy-5-octadecene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 87 percent / potassium hexamethyldisilylamide / tetrahydrofuran; toluene / 3 h / -84 °C

2.1: 2,6-tert-butyl-4-methylpyridine; trifluoromethanesufonic anhydride; dimethyl sulfide / CH₂Cl₂ / 1.5 h / -45 - 20 °C

2.2: 55 percent / CH₂Cl₂ / 10 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; dimethylsulfide; trifluoromethylsulfonic anhydride; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo051518u