(2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol
• CAS No.: 1089188-04-4
• Molecular Formula: C₅₇H₁₀₅N₃O₉
• Molecular Weight: 976.475
• Mol file: 1089188-04-4.mol

Synonyms:(2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol

Chemical Property of (2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol

There total 16 articles about (2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol 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%

phenyl isocyanate (103-71-9) + (2S,3S,4R)-1-O-(6-deoxy-6-amino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol (424823-18-7) → (2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol (1089188-04-4)

Guidance literature:

In N,N-dimethyl-formamide; at 20 - 25 ℃; for 1.08333h; Inert atmosphere;

DOI:10.1021/jo102064p

Reference yield:

C92H135N3O9 → (2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol (1089188-04-4)

Guidance literature:

With hydrogen; palladium; In ethanol; chloroform; for 5h; under 760.051 Torr;

DOI:10.1021/ja8064182

Reference yield:

(2S,3S,4R)-2-[(N-tert-butoxycarbonyl)amino]-3,4-di-tert-butyldimethylsilyloxy-1-O-(2,3,4,6-tetrakis-O-trimethylsilyl-α-D-galactopyranosyl)octadecane (1260236-37-0) → (2S,3S,4R)-1-O-(6-deoxy-6-phenylaminocarbonylamino-α-D-galactopyranosyl)-2-[(N-hexacosanoyl)amino]octadecane-3,4-diol (1089188-04-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetic acid / methanol; acetone / 0 - 25 °C / Inert atmosphere

2.1: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 0 - 25 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 0.58 h / 20 - 25 °C / Inert atmosphere

4.1: trifluoroacetic acid / 0.58 h / 20 - 25 °C / Inert atmosphere

5.1: sodium acetate / tetrahydrofuran; water / 2 h / 20 - 25 °C / Inert atmosphere

6.1: trimethylphosphane / tetrahydrofuran / 5 h / 20 - 25 °C / Inert atmosphere

6.2: 1 h / 20 - 25 °C / Inert atmosphere

7.1: N,N-dimethyl-formamide / 1.08 h / 20 - 25 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; sodium acetate; acetic acid; triphenylphosphine; trifluoroacetic acid; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 2.1: Mitsunobu reaction / 6.1: Staudinger reaction / 6.2: Staudinger reaction;

DOI:10.1021/jo102064p

upstream raw materials:

(2S,3S,4R)-1,3,4-tris-(tert-butyldimethylsilanyloxy)-2-(N-tert-butoxycarbonyl)aminooctadecane

(1'S,2'S,3'R)-[2,3-bis-(tert-butyldimethylsilanyloxy)-1-(hydroxymethyl)heptadecyl]carbamic acid tert-butyl ester

(2S,3S,4R)-2-[(N-tert-butoxycarbonyl)amino]-3,4-di-tert-butyldimethylsilyloxy-1-O-(2,3,4,6-tetrakis-O-trimethylsilyl-α-D-galactopyranosyl)octadecane

(2S,3S,4R)-2-[(N-tert-butoxycarbonyl)amino]-3,4-di-tert-butyldimethylsilyloxy-1-O-(2,3,4-tri-O-trimethylsilyl-α-D-galactopyranosyl)octadecane