(2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

Base Information

• Chemical Name: (2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane
• CAS No.: 321734-88-7
• Molecular Formula: C₆₆H₈₅NO₈
• Molecular Weight: 1020.4
• Mol file: 321734-88-7.mol

Synonyms:(2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

Chemical Property of (2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

There total 3 articles about (2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)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: 80.0%

(2S,3R,4S,5S,6R)-2-((2S,3R,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran (321735-10-8) → (2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (321734-88-7)

Guidance literature:

With hydrogen; Lindlar's catalyst; In ethanol; ethyl acetate; for 12h; under 760 Torr;

DOI:10.1016/S0957-4166(00)00366-9

Reference yield:

Methanesulfonic acid (E)-(1R,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-5-enyl ester → (2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (321734-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / tosylhydrazide; aq. NaOAc / ethanol / 5 h / Heating

2: 84 percent / NaN₃ / dimethylsulfoxide / 36 h / 100 °C

3: 80 percent / H₂ / 5 percent Pd/CaCO₃ / ethanol; ethyl acetate / 12 h / 760 Torr

With sodium azide; hydrogen; sodium acetate; toluene-4-sulfonic acid hydrazide; Lindlar's catalyst; In ethanol; dimethyl sulfoxide; ethyl acetate; 1: Reduction / 2: Substitution / 3: Hydrogenation;

DOI:10.1016/S0957-4166(00)00366-9

Reference yield:

Methanesulfonic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecyl ester (321735-08-4) → (2S,3R,4R)-2-amino-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)octadecane (321734-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / NaN₃ / dimethylsulfoxide / 36 h / 100 °C

2: 80 percent / H₂ / 5 percent Pd/CaCO₃ / ethanol; ethyl acetate / 12 h / 760 Torr

With sodium azide; hydrogen; Lindlar's catalyst; In ethanol; dimethyl sulfoxide; ethyl acetate; 1: Substitution / 2: Hydrogenation;

DOI:10.1016/S0957-4166(00)00366-9

upstream raw materials:

(2S,3R,4S,5S,6R)-2-((2S,3R,4R)-2-Azido-3,4-bis-benzyloxy-octadecyloxy)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran

Methanesulfonic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecyl ester

Downstream raw materials:

(2S,3R,4R)-3,4-di-O-benzyl-1-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-2-N-docosanoyl-octadecane