(2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene

Base Information

Chemical Name:(2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene
CAS No.:206856-96-4
Molecular Formula:C₅₈H₇₉N₃O₁₃
Molecular Weight:1026.28
Hs Code.:

Synonyms:(2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene

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Chemical Property of (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene

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Technology Process of (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene

There total 12 articles about (2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-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: 64.0%

: 103348-50-1
(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol

: 206856-94-2
ethyl 2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 206856-96-4
(2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene

: 206856-95-3
(2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranosyloxy]-4-octadecene

Guidance literature:: (2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol; ethyl 2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; In 1,4-dioxane; at 22 ℃;

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In 1,4-dioxane;
DOI:10.1016/S0968-0896(01)00015-3

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 206856-96-4
(2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / p-toluenesulfonic acid / acetonitrile / 22 °C

2.1: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂; pyridine / 22 °C

3.1: 2,6-di-tert-butyl-4-methylpyridine / dioxane / 22 °C

3.2: 24 percent / dimethyl(methylthio)sulfonium triflate / dioxane

With dmap; 2,6-di-tert-butyl-4-methylpyridine; toluene-4-sulfonic acid; In 1,4-dioxane; pyridine; dichloromethane; acetonitrile;
DOI:10.1016/S0968-0896(01)00015-3

Reference yield:

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

: 206856-96-4
(2S,3R,4E)-3-benzoyloxy-2-azido-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / pyridine / 5 h

2.1: 92 percent / NaH / dimethylformamide / 1 h

3.1: 80 percent / LiAlH₄ / tetrahydrofuran / 2 h

4.1: 97 percent / Et₃N / CH₂Cl₂ / 0.5 h

5.1: NaH; KI / dimethylformamide; tetrahydrofuran / 12 h / 65 °C

6.1: 0.069 g / Bu₄NF / tetrahydrofuran / 22 °C

7.1: 93 percent / aq. HCl / tetrahydrofuran / 12 h / 22 °C

8.1: 89 percent / p-toluenesulfonic acid / acetonitrile / 22 °C

9.1: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂; pyridine / 22 °C

10.1: 2,6-di-tert-butyl-4-methylpyridine / dioxane / 22 °C

10.2: 24 percent / dimethyl(methylthio)sulfonium triflate / dioxane

With hydrogenchloride; dmap; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; potassium iodide; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0968-0896(01)00015-3