(3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate

Base Information

Chemical Name:(3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate
CAS No.:1349697-01-3
Molecular Formula:C₃₃H₅₁NO₆Si₂
Molecular Weight:613.942
Hs Code.:

Synonyms:(3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate

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Chemical Property of (3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate

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Technology Process of (3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate

There total 8 articles about (3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate 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: 85.0%

: (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-di-hydro-4H-1,3-oxazine

: 501-53-1,94274-21-2
benzyl chloroformate

: 1349697-01-3
(3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate

Guidance literature:: (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-di-hydro-4H-1,3-oxazine; With sodium hydrogencarbonate; In dichloromethane; water; Cooling with ice;

benzyl chloroformate; In dichloromethane; water; at 20 ℃; for 48h;
DOI:10.1016/j.tetasy.2013.11.009

Reference yield: 78.0%

: 1349697-11-5
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

: 501-53-1,94274-21-2
benzyl chloroformate

: 1349697-01-3
(3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate

Guidance literature:: With water; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 48h; Cooling with ice;
DOI:10.1016/j.tet.2011.09.084

Reference yield:

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

: 1349697-01-3
(3R,4R,5R)-5-(benzyloxycarbonylamino)-4,6-bis(tert-butyldimethylsilyloxy)hex-1-en-3-yl benzoate

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: -78 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 °C

3.2: 5 h / 0 °C

4.1: water; sodium hydrogencarbonate / dichloromethane / 48 h / 20 °C / Cooling with ice

With 1H-imidazole; water; sodium hydride; sodium hydrogencarbonate; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; mineral oil; 4.1: Schotten-Baumann reaction;
DOI:10.1016/j.tet.2011.09.084