(4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

Base Information

Chemical Name:(4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one
CAS No.:1378893-42-5
Molecular Formula:C₁₉H₂₅NO₄
Molecular Weight:331.412
Hs Code.:

Synonyms:(4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

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Chemical Property of (4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

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Technology Process of (4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

There total 3 articles about (4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one 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: 49.0%

: (4S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-1,3-oxazinan-6-one

: 106-95-6
allyl bromide

: 1378893-42-5
(4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

Guidance literature:: (4S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-1,3-oxazinan-6-one; With potassium hexamethylsilazane; In toluene; at -78 ℃; for 0.666667h; Inert atmosphere;

allyl bromide; In toluene; at -78 - -40 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2012.04.012

Reference yield:

: 1378893-18-5
(4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-allyl-1,3-oxazinan-6-one

: 333-27-7
methyl trifluoromethanesulfonate

: 1378893-42-5
(4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

: 1378893-45-8
(4S,5R)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

Guidance literature:: (4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-allyl-1,3-oxazinan-6-one; With potassium hexamethylsilazane; In toluene; at -78 ℃; for 0.666667h; Inert atmosphere;

methyl trifluoromethanesulfonate; In toluene; at -78 - -40 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2012.04.012

Reference yield:

: 914939-74-5
phenylmethyl (4R)-4-(1-methylethyl)-6-oxo-1,3-oxazinane-3-carboxylate

: 1378893-42-5
(4S,5S)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

: 1378893-45-8
(4S,5R)-N-benzyloxycarbonyl-4-isopropyl-5-methyl-5-allyl-1,3-oxazinan-6-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hexamethylsilazane / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; toluene / 0.67 h / -78 °C / Inert atmosphere

1.2: -78 - -15 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / toluene / 0.67 h / -78 °C / Inert atmosphere

2.2: -78 - -40 °C / Inert atmosphere

With potassium hexamethylsilazane; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; toluene;
DOI:10.1016/j.tet.2012.04.012