(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

Base Information

• Chemical Name: (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
• CAS No.: 321735-10-8
• Molecular Formula: C₆₆H₈₃N₃O₈
• Molecular Weight: 1046.4
• Mol file: 321735-10-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 2 articles about (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 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: 84.0%

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,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)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 100 ℃; for 36h;

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,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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium azide; sodium acetate; toluene-4-sulfonic acid hydrazide; In ethanol; dimethyl sulfoxide; 1: Reduction / 2: Substitution;

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

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

upstream raw materials:

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

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