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

Base Information

Chemical Name:(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene
CAS No.:206857-32-1
Molecular Formula:C₆₉H₁₁₁NO₁₃
Molecular Weight:1162.64
Hs Code.:

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

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

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

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

There total 11 articles about (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-4,6-O-benzylidene-α-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: 90.0%

: 206857-31-0
(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-2-O-p-methoxybenzyl-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene

: 206857-32-1
(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 5 - 23 ℃; for 1.5h;
DOI:10.1016/S0968-0896(01)00015-3

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 206857-32-1
(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 62 percent / p-toluenesulfonic acid / acetonitrile / 22 °C

2.1: 59 percent / NaH / dimethylformamide / 22 °C

3.1: 82 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran; dimethylformamide / 50 - 60 °C

4.1: 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / 22 °C

4.2: 39 percent / dimethyl(methylthio)sulfonium triflate / acetonitrile

5.1: H₂S / pyridine; H₂O

5.2: 83 percent / aq. AcONa / tetrahydrofuran / 22 °C

6.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1.5 h / 5 - 23 °C

With 2,6-di-tert-butyl-4-methylpyridine; hydrogen sulfide; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0968-0896(01)00015-3

Reference yield:

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

: 206857-32-1
(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / pyridine / 5 h

2.1: 64 percent / NaH / dimethylformamide / 2 h / 22 °C

3.1: 78 percent / aq. AcOH / 1.5 h / 60 °C

4.1: 62 percent / p-toluenesulfonic acid / acetonitrile / 22 °C

5.1: 59 percent / NaH / dimethylformamide / 22 °C

6.1: 82 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran; dimethylformamide / 50 - 60 °C

7.1: 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / 22 °C

7.2: 39 percent / dimethyl(methylthio)sulfonium triflate / acetonitrile

8.1: H₂S / pyridine; H₂O

8.2: 83 percent / aq. AcONa / tetrahydrofuran / 22 °C

9.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1.5 h / 5 - 23 °C

With 2,6-di-tert-butyl-4-methylpyridine; hydrogen sulfide; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0968-0896(01)00015-3