(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol

Base Information

Chemical Name:(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol
CAS No.:115018-44-5
Molecular Formula:C₄₃H₇₁NO₆
Molecular Weight:698.04
Hs Code.:

Synonyms:(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol

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Chemical Property of (2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol

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Technology Process of (2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol

There total 9 articles about (2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-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: 64.0%

: 88195-82-8
p-nitrophenyl 2-O-acetyl-(2R)-2-hydroxypalmitate

: 115031-70-4
1-O-benzoylsphingadiene hydrochloride

: 115018-44-5
(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol

Guidance literature:: In pyridine; at 50 ℃; for 19h;

Reference yield: 41.0%

: 220869-82-9
(4R,5S,2'R)-3-(2'-acetoxyhexadecanoyl)-4-methyl-5-phenyl-1,3-oxazolidine-2-thione

: 262592-91-6
(4S,1'R,2'E,5'RS,6'E)-2-phenyl-4-(5'-phenylsulfonyl-1'-trimethylsilyloxyhexadeca-2',6'-dienyl)-4,5-dihydrooxazole

: 115018-44-5
(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol

Guidance literature:: (4S,1'R,2'E,5'RS,6'E)-2-phenyl-4-(5'-phenylsulfonyl-1'-trimethylsilyloxyhexadeca-2',6'-dienyl)-4,5-dihydrooxazole; With 1,3-bis-(diphenylphosphino)propane; lithium triethylborohydride; palladium diacetate; at 0 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 15h;

(4R,5S,2'R)-3-(2'-acetoxyhexadecanoyl)-4-methyl-5-phenyl-1,3-oxazolidine-2-thione; With triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 5h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(99)01018-2

Reference yield:

: 173531-24-3
(4S,1'S,2'R)-4-(1',2'-Epoxybut-3'-enyl)-2-phenyl-4,5-dihydrooxazole

: 115018-44-5
(2S,3R,4E,8E,2'R)-2-(2'-acetoxyhexadecanoyl)amino-1-O-benzoyl-4,8-octadiene-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / LiBr / acetonitrile / 3 h / 5 - 10 °C

2.1: 71 percent / n-BuLi / tetrahydrofuran; hexane / -40 - 10 °C

3.1: LiBEt₃H; dppp / Pd(OAc)2 / 1 h / 0 °C

3.2: aq. HCl / tetrahydrofuran / 15 h / 20 °C

3.3: 41 percent / Et₃N / dimethylformamide / 5 h / 60 °C

With n-butyllithium; 1,3-bis-(diphenylphosphino)propane; lithium triethylborohydride; lithium bromide; palladium diacetate; In tetrahydrofuran; hexane; acetonitrile; 1.1: Ring cleavage / 2.1: Substitution / 3.1: desulfonylation / 3.2: Ring cleavage / 3.3: Acylation;
DOI:10.1016/S0040-4020(99)01018-2