(2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol

Base Information

• Chemical Name: (2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol
• CAS No.: 173067-89-5
• Molecular Formula: C₃₆H₅₅Cl₂NO₃Si
• Molecular Weight: 648.829
• Mol file: 173067-89-5.mol

Synonyms:(2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol

Chemical Property of (2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol

There total 2 articles about (2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-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: 95.0%

tert-butylchlorodiphenylsilane (58479-61-1) + N-dichloroacetylsphingosine (80692-62-2) → (2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol (173067-89-5)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; dichloromethane; for 7h; Ambient temperature;

DOI:10.1016/0008-6215(95)00189-Z

Reference yield:

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → (2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol (173067-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-diisopropylethylamine, aliquots / methanol; CH₂Cl₂

2: 95 percent / Et₃N, N,N-dimethylaminopyridine / CH₂Cl₂; tetrahydrofuran / 7 h / Ambient temperature

With dmap; aliquots; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0008-6215(95)00189-Z

Reference yield: 96.0%

benzoyl chloride (98-88-4) + (2S,3R,4E)-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol (173067-89-5) → (2S,3R,4E)-3-O-benzoyl-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol (173067-90-8)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1016/0008-6215(95)00189-Z

upstream raw materials:

tert-butylchlorodiphenylsilane

N-dichloroacetylsphingosine

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

Downstream raw materials:

(2S,3R,4E)-3-O-benzoyl-1-O-tert-butyldiphenylsilyl-2-dichloroacetamido-4-octadecen-1,3-diol

(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octadecen-1,3-diol

Benzoic acid (E)-(R)-1-[(R)-1-(2,2-dichloro-acetylamino)-2-iodo-ethyl]-hexadec-2-enyl ester

(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-1-O-methylsulfonyl-4-octadecen-1,3-diol