(5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester

Base Information

Chemical Name:(5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester
CAS No.:209160-55-4
Molecular Formula:C₁₈H₂₃NO₅
Molecular Weight:333.384
Hs Code.:

Synonyms:(5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester

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Chemical Property of (5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester

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Technology Process of (5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester

There total 7 articles about (5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester 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:

: 209160-59-8
(5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid benzyl ester

: 209160-55-4
(5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / H₂ / Pd/C / ethanol / 1.5 h / Ambient temperature

2: oxalyl chloride / CH₂Cl₂ / 4 h / Heating

3: 2 h / Ambient temperature

With oxalyl dichloride; hydrogen; palladium on activated charcoal; In ethanol; dichloromethane;
DOI:10.1021/jo9722414

Reference yield:

: 181528-70-1
(2R,3S,6S)-6-Furan-3-yl-2-hydroxymethyl-3-methyl-piperidin-4-one

: 209160-55-4
(5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / Et₃N / tetrahydrofuran / 0.5 h / 0 °C

2: 1.) K-Selectride, 2.) NaOH, aq. H₂O₂ / 1.) THF, -80 deg C, 2.) EtOH, 20 min

3: 83 percent / NaH / dimethylformamide / 4 h / 120 °C

4: aq. H₂O₂, NaOH, O₃/O₂ / CH₂Cl₂; methanol / 1 h / Ambient temperature

5: oxalyl chloride / CH₂Cl₂ / 4 h / Heating

6: 2 h / Ambient temperature

With sodium hydroxide; oxalyl dichloride; dihydrogen peroxide; oxygen; sodium hydride; potassium tri-sec-butyl-borohydride; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9722414

Reference yield:

: 209160-35-0
(-)-(2S,4R,5S,6R)-1-aza-2-(3-furyl)-4-hydroxy-5-methyl-8-oxa-9-oxobicyclo[4.3.0]nonane

: 209160-55-4
(5S,7R,8S,8aR)-7-Benzyloxy-8-methyl-3-oxo-hexahydro-oxazolo[3,4-a]pyridine-5-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / NaH / dimethylformamide / 4 h / 120 °C

2: aq. H₂O₂, NaOH, O₃/O₂ / CH₂Cl₂; methanol / 1 h / Ambient temperature

3: oxalyl chloride / CH₂Cl₂ / 4 h / Heating

4: 2 h / Ambient temperature

With sodium hydroxide; oxalyl dichloride; dihydrogen peroxide; oxygen; sodium hydride; ozone; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo9722414