(2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol

Base Information

• Chemical Name: (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol
• CAS No.: 160280-69-3
• Molecular Formula: C₇₇H₁₁₅NO₄
• Molecular Weight: 1118.76
• Mol file: 160280-69-3.mol

Synonyms:(2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol

Chemical Property of (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol

There total 9 articles about (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol 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: 88.0%

1-hexacosanoic acid (506-46-7) + (1S,2S,3R)-2,3-Bis-benzyloxy-1-trityloxymethyl-heptadecylamine (160280-68-2) → (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol (160280-69-3)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 2h; Heating;

DOI:10.1271/bbb.60.288

Reference yield:

benzyl chloride (100-44-7) → (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol (160280-69-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / dimethylformamide / 18 h / Ambient temperature

2: 98 percent / ammonium formate / Pd/C / methanol; propan-1-ol / 16 h / Ambient temperature

3: 88 percent / WSC-HCl / CH₂Cl₂ / 2 h / Heating

With ammonium formate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; propan-1-ol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb.60.288

Reference yield:

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol (117168-59-9) → (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol (160280-69-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / pyridine / CH₂Cl₂ / 16 h / Ambient temperature

2: NaH / dimethylformamide / 18 h / Ambient temperature; 0-deg C -> rt

3: 98 percent / ammonium formate / Pd/C / methanol; propan-1-ol / 16 h / Ambient temperature

4: 88 percent / WSC-HCl / CH₂Cl₂ / 2 h / Heating

With pyridine; ammonium formate; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; propan-1-ol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb.60.288

upstream raw materials:

1-hexacosanoic acid

(1S,2S,3R)-2,3-Bis-benzyloxy-1-trityloxymethyl-heptadecylamine

benzyl chloride

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

Downstream raw materials:

(2S,3S,4R)-2-hexacosylamino-3,4-di-O-benzyl-1,3,4-octadecanetriol

Refernces

• 1、 Morita, Masahiro,Sawa, Eiji,Yamaji, Kazuo,Sakai, Teruyuki,Natori, Takenori,Koezuka, Yasuhiko,Fukushima, Hideaki,Akimoto, Kohji. "Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4- octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylceramide, KRN7000". . p. 288 - 292. Retrieved 2007/10/03.