(5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

Base Information

Chemical Name:(5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one
CAS No.:675130-50-4
Molecular Formula:C₂₃H₂₇NO₄
Molecular Weight:381.472
Hs Code.:

Synonyms:(5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

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Chemical Property of (5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

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Technology Process of (5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

There total 5 articles about (5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-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: 93.0%

: 100-39-0
benzyl bromide

: 675130-49-1
(5R,7S,8S,8aR)-5-Ethyl-7,8-dihydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one

: 675130-50-4
(5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4.5h;
DOI:10.1021/jo035522m

Reference yield: 39.0%

: 74808-10-9
O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

: 675130-51-5
(2R,3S,4S,6R)-3,4-Bis-benzyloxy-6-ethyl-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

: 675130-50-4
(5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

: 675130-52-6
(2R,3S,4S,6R)-3,4-Bis-benzyloxy-6-ethyl-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 2h;
DOI:10.1021/jo035522m

Reference yield:

: 675130-42-4,675130-54-8
(5R,8aS)-5-ethyl-4,5,6,8a-tetrahydrooxazolidino[3,4-a]pyridin-3-one

: 675130-50-4
(5R,7S,8S,8aR)-7,8-Bis-benzyloxy-5-ethyl-hexahydro-oxazolo[3,4-a]pyridin-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / mCPBA / CH₂Cl₂ / 72 h / 20 °C

2.1: AcOH / 17 h / 100 °C

2.2: 615 mg / K₂CO₃ / methanol; H₂O / 3 h / 20 °C

3.1: 93 percent / NaH / dimethylformamide / 4.5 h / 20 °C

With sodium hydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035522m