N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

Base Information

Chemical Name:N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide
CAS No.:1029529-75-6
Molecular Formula:C₁₉H₃₀ClNO₃Si
Molecular Weight:383.991
Hs Code.:

Synonyms:N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

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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 N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

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Technology Process of N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

There total 5 articles about N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide 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: 96.0%

: (4R,5R)-4-((tert-butyldimethylsilyloxy)methyl)-5-((E)-3-chloroprop-1-enyl)-2-phenyl-4,5-dihydrooxazole

: 1029529-75-6
N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

Guidance literature:: With hydrogenchloride; water; In tetrahydrofuran; methanol; at 20 ℃; for 12h;
DOI:10.1039/b717961h

Reference yield:

: 1029529-50-7
(R,E)-N-(1-(tert-butyldimethylsilyloxy)-6-chloro-3-oxohex-4-en-2-yl)benzamide

: 1029529-75-6
N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

: 1029529-52-9
N-((2R,3S,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

Guidance literature:: With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; ethanol; at -78 ℃; for 2h; optical yield given as %de;
DOI:10.1039/b717961h

Reference yield:

(R)-methyl 2-benzamido-3-(tert-butyldimethylsilyloxy)propanoate: 1029529-45-0
(R)-methyl 2-benzamido-3-(tert-butyldimethylsilyloxy)propanoate

: 1029529-75-6
N-((2R,3R,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

: 1029529-52-9
N-((2R,3S,E)-1-(tert-butyldimethylsilyloxy)-6-chloro-3-hydroxyhex-4-en-2-yl)benzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: trimethylaluminum / hexane; dichloromethane / 0.5 h / 20 °C

1.2: 1 h / 20 °C

2.1: methyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 0.5 h / -78 °C

3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; ethanol / 2 h / -78 °C

3.2: -78 °C

With methyllithium; trimethylaluminum; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane;
DOI:10.1016/j.tet.2011.09.084