(2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol

Base Information

Chemical Name:(2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol
CAS No.:1416052-13-5
Molecular Formula:C₈₈H₁₆₁NO₅Si₂
Molecular Weight:1369.42
Hs Code.:

Synonyms:(2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol

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Chemical Property of (2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol

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Technology Process of (2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol

There total 9 articles about (2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-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: 91.0%

: 1416052-11-3
(2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-hydroxy)triacontanamido]octadec-4-ene-1,3-diol

: 112-76-5
Stearoyl chloride

: 1416052-13-5
(2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol

Guidance literature:: With pyridine; In chloroform; at 0 - 20 ℃; for 0.75h;
DOI:10.1271/bbb.120333

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 1416052-13-5
(2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine / 0.25 h / 0 °C

2.1: trimethylphosphane / tetrahydrofuran / 17 h / 20 °C

2.2: 2 h / 20 °C

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 19 h / 20 °C

4.1: potassium carbonate; methanol / dichloromethane / 18 h / 20 °C

5.1: pyridine / chloroform / 0.75 h / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; methanol; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trimethylphosphane; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1271/bbb.120333

Reference yield:

: 1416052-09-9
(2S,3R,4E)-2-amino-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)octadec-4-ene-1,3-diol

: 1416052-13-5
(2S,3R,4E)-3-O-(tert-butyldimethylsilyl)-1-O-(tert-butyldiphenylsilyl)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 19 h / 20 °C

2: potassium carbonate; methanol / dichloromethane / 18 h / 20 °C

3: pyridine / chloroform / 0.75 h / 0 - 20 °C

With pyridine; methanol; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; chloroform;
DOI:10.1271/bbb.120333