(1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol

Base Information

Chemical Name:(1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol
CAS No.:1333237-22-1
Molecular Formula:C₃₃H₅₆Cl₂O₅Si₂
Molecular Weight:659.882
Hs Code.:

(1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol

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Chemical Property of (1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol

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Technology Process of (1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol

There total 6 articles about (1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol 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:

: C₃₃H₅₇Cl₃O₅Si₂

: 1333237-21-0
(((2S,3S)-3-((E)-3-((2S,3S)-3-((1R,4R,5S)-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-chlorohexyl)oxiran-2-yl)-1-chloroprop-1-enyl)oxiran-2-yl)methoxy)(tert-butyl)dimethylsilane

: 1333237-22-1
(1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol

Guidance literature:: C₃₃H₅₇Cl₃O₅Si₂; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 4.5h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; mineral oil; at 0 ℃; Inert atmosphere;
DOI:10.1002/anie.201102521

Reference yield:

: ((2S,3S)-3-((1R,2S,4S,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

: 1333237-21-0
(((2S,3S)-3-((E)-3-((2S,3S)-3-((1R,4R,5S)-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-chlorohexyl)oxiran-2-yl)-1-chloroprop-1-enyl)oxiran-2-yl)methoxy)(tert-butyl)dimethylsilane

: 1333237-22-1
(1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: methanol; potassium carbonate / 0.17 h / 0 °C / Inert atmosphere

2.1: pyridine; pyridine hydrofluoride / acetonitrile / 45 h / 0 - 20 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / -78 - -40 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 2.42 h / 0 - 20 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 4.5 h / 0 - 20 °C / Inert atmosphere

5.2: 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; methanol; pyridine hydrofluoride; sodium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane; acetonitrile; mineral oil;
DOI:10.1002/anie.201102521

Reference yield:

: 1333237-06-1
((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methanol

: 1333237-21-0
(((2S,3S)-3-((E)-3-((2S,3S)-3-((1R,4R,5S)-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-chlorohexyl)oxiran-2-yl)-1-chloroprop-1-enyl)oxiran-2-yl)methoxy)(tert-butyl)dimethylsilane

: 1333237-22-1
(1E,4S,5Z,9R,10S)-9-(benzyloxy)-10-(tert-butyldimethylsilyloxy)-1-((2S,3S)-3-((tert-butyldimethylsilyloxy)methyl)oxiran-2-yl)-1,5-dichloroundeca-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine; pyridine hydrofluoride / acetonitrile / 45 h / 0 - 20 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / -78 - -40 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 2.42 h / 0 - 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 4.5 h / 0 - 20 °C / Inert atmosphere

4.2: 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; pyridine hydrofluoride; sodium hydride; In tetrahydrofuran; dichloromethane; acetonitrile; mineral oil;
DOI:10.1002/anie.201102521