(3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Base Information

Chemical Name:(3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine
CAS No.:1253265-72-3
Molecular Formula:C₂₄H₃₁NO₄
Molecular Weight:397.514
Hs Code.:

Synonyms:(3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

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Chemical Property of (3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

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Technology Process of (3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

There total 4 articles about (3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 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:

: 1253265-22-3
(3R,8S,8aR)-8-allyl-6-(tert-butoxycarbonyl)-5-oxo-3-phenyl-2,3,8,8a-tetrahydro-5H-oxazolo[3,2-a]pyridine

: 1730-25-2
allylmagnesium bromide

: 1253265-74-5
(3R,6R,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 1253265-72-3
(3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Guidance literature:: With copper(l) iodide; chloro-trimethyl-silane; lithium chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 18h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201000421

Reference yield:

: 864967-32-8
(3R,8R,8aR)-8-allyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 1253265-74-5
(3R,6R,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 1253265-72-3
(3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

1.2: 1.5 h / -78 °C / Inert atmosphere

1.3: 1 h / Inert atmosphere

2.1: dihydrogen peroxide; pyridine / water; dichloromethane / 2 h / 20 °C

3.1: lithium chloride; copper(l) iodide; chloro-trimethyl-silane / tetrahydrofuran; diethyl ether / 20 h / -78 °C / Inert atmosphere

With pyridine; copper(l) iodide; chloro-trimethyl-silane; dihydrogen peroxide; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1002/anie.201402263

Reference yield:

: (3R,8S,8aR)-8-allyl-6-(tert-butoxycarbonyl)-5-oxo-3-phenyl-6-(phenylselenyl)-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 1253265-74-5
(3R,6R,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

: 1253265-72-3
(3R,6S,7R,8S,8aR)-6-(tert-butoxycarbonyl)-7,8-diallyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine

Guidance literature:: Multi-step reaction with 2 steps

1: dihydrogen peroxide; pyridine / water; dichloromethane / 2 h / 20 °C

2: lithium chloride; copper(l) iodide; chloro-trimethyl-silane / tetrahydrofuran; diethyl ether / 20 h / -78 °C / Inert atmosphere

With pyridine; copper(l) iodide; chloro-trimethyl-silane; dihydrogen peroxide; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1002/anie.201402263