(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

Base Information

Chemical Name:(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene
CAS No.:206857-68-3
Molecular Formula:C₇₁H₁₂₅NO₁₃Si
Molecular Weight:1228.86
Hs Code.:

(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

Synonyms:(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

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Technology Process of (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

There total 7 articles about (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene 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: 73.0%

: 206857-68-3
(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

Guidance literature:

Reference yield: 69.0%

: 206857-67-2
(2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

: 112-67-4
n-hexadecanoyl chloride

: 206857-68-3
(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

Guidance literature:: (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene; With hydrogen sulfide; In pyridine; water;

n-hexadecanoyl chloride; With sodium acetate; In tetrahydrofuran; at 22 ℃;
DOI:10.1016/S0968-0896(01)00015-3

Reference yield:

: 172146-95-1
ethyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

: 206857-68-3
(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(5,5-di-tert-butyloxycarbonylpentyl)-3,4-O-isopropylidene-6-O-tert-butyldimethylsilyl-β-D-galactopyranosyloxy]-4-octadecene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / pyridine / 5 h

2.1: 79 percent / NaH / dimethylformamide / 0.5 h / 22 °C

3.1: 100 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran; dimethylformamide / 2 h / 50 - 60 °C

4.1: 2,6-di-tert-butyl-4-methylpyridine / toluene / 1 h / 22 °C

4.2: 21 percent / dimethyl(methylthio)sulfonium triflate / toluene / 1 h

5.1: H₂S / H₂O; pyridine

5.2: 69 percent / aq. NaOAc / tetrahydrofuran / 22 °C

With 2,6-di-tert-butyl-4-methylpyridine; hydrogen sulfide; potassium tert-butylate; sodium hydride; In tetrahydrofuran; pyridine; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/S0968-0896(01)00015-3