Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside

Base Information

Chemical Name:Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside
CAS No.:161128-59-2
Molecular Formula:C₄₀H₄₂N₄O₆S
Molecular Weight:706.863
Hs Code.:

Synonyms:Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside

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Chemical Property of Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside

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Technology Process of Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside

There total 3 articles about Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside 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:

: 100-39-0
benzyl bromide

: 161128-62-7
Methyl 3-azido-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside

: 161128-59-2
Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h; Yield given;
DOI:10.1016/S0957-4166(00)86296-5

Reference yield:

: (3SR,4R,5R,6S,7S)-3-Azido-8-O-tert-butyldiphenylsilyl-4,5,6,7,8-pentahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-1-octanone

: 161128-59-2
Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 50 percent / HCl / 14 h / 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: dimethylformamide / 0.5 h / 20 °C

With hydrogenchloride; sodium hydride; In N,N-dimethyl-formamide; 1.1: Cyclization / 2.1: Metallation / 2.2: Etherification;

Reference yield:

: 154796-68-6
(4R,5R,6S,7S)-8-(O-tert-butyldiphenylsilyl)-4,5,6,7,8-pentahydroxy-4,6:5,7-di-O-isopropylidene-1-(2-thiazolyl)-2(E)-octen-1-one

: 161128-59-2
Methyl 3-azido-4,6,7,8-tetra-O-benzyl-2,3-dideoxy-1-(2-thiazolyl)-β-D-glycero-D-galacto-octopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: Me₃SiN₃, Bu₄NF / CH₂Cl₂ / 96 h / -20 °C

2: 2percent HCl/MeOH / 14 h / Ambient temperature

3: NaH / dimethylformamide / 1 h / 0 °C

With hydrogenchloride; methanol; trimethylsilylazide; tetrabutyl ammonium fluoride; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(00)86296-5