(2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane

Base Information

• Chemical Name: (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane
• CAS No.: 1542131-42-9
• Molecular Formula: C₅₂H₇₅N₃O₅Si
• Molecular Weight: 850.27

Synonyms:(2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane

Chemical Property of (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane

Chemical Property:

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Technology Process of (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane

There total 1 articles about (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane 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: 100.0%

(2R,3S,4S,5S,6R)-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecan-2-ol (1542131-41-8) → (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane (1542131-42-9)

Guidance literature:

With diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.bmc.2013.12.009

Reference yield: 96.0%

(2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane (1542131-42-9) → (2S,3S,4S,5S,6R)-2-azido-3,4,5,6-(tetrabenzyloxy)octadecan-1-ol (1542131-43-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.833333h;

DOI:10.1016/j.bmc.2013.12.009

Reference yield:

(2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane (1542131-42-9) → (2S,3S,4S,5S,6R)-2-azido-3,4,5,6-(tetrabenzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-α-d-galactopyranoside (1542131-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.83 h / 20 °C

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

2.2: 16 h / 20 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2013.12.009

upstream raw materials:

(2R,3S,4S,5S,6R)-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecan-2-ol

Downstream raw materials:

(2S,3S,4S,5S,6R)-2-azido-3,4,5,6-(tetrabenzyloxy)octadecan-1-ol

(2S,3S,4S,5S,6R)-2-azido-3,4,5,6-(tetrabenzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-α-d-galactopyranoside

(2S,3S,4S,5S,6R)-2-amino-3,4,5,6-(tetrabenzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-α-d-galactopyranoside

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