(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

Base Information

• Chemical Name: (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
• CAS No.: 1542131-45-2
• Molecular Formula: C₇₄H₁₀₁NO₁₀Si
• Molecular Weight: 1192.7
• Mol file: 1542131-45-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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: 71.0%

(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) + trimethylphosphane (594-09-2) → (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 (1542131-45-2)

Guidance literature:

(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; trimethylphosphane; In tetrahydrofuran; at 20 ℃; for 2h;

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 2h;

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-amino-3,4,5,6-(tetrabenzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-α-d-galactopyranoside (1542131-45-2)

Guidance literature:

Multi-step reaction with 3 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

3.1: tetrahydrofuran / 2 h / 20 °C

3.2: 2 h / 20 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2013.12.009

Reference yield:

2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylidene)-α,β-D-galactopyranose → (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 (1542131-45-2)

Guidance literature:

Multi-step reaction with 3 steps

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

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

2.2: 16 h / 20 °C

3.1: tetrahydrofuran / 2 h / 20 °C

3.2: 2 h / 20 °C

With caesium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2013.12.009

upstream raw materials:

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

(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

trimethylphosphane

Downstream raw materials:

(2S,3S,4S,5S,6R,2'R,3'R)-2-[2',3'-(isopropylidenedioxy)hexacosanoylamino]-3,4,5,6-(tetrabenzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-α-d-galactopyranoside