[(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride

Base Information

Chemical Name:[(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride
CAS No.:1054655-93-4
Molecular Formula:C₂₂H₂₈ClNO₄
Molecular Weight:405.922
Hs Code.:

Synonyms:[(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride

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Chemical Property of [(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride

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Technology Process of [(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride

There total 9 articles about [(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride 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:

: 264218-62-4
(1R,1'S,5R,8aR)-3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl acetic acid methyl ester

: 1054655-93-4
[(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride

Guidance literature:: With sodium hydroxide; oxalyl dichloride; In dichloromethane; at 20 ℃;
DOI:10.1021/ol0056271

Reference yield:

: [(1R,5R,8aS)-1-((S)-1-Benzyloxy-hexyl)-3,7-dioxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester

: 1054655-93-4
[(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride

Guidance literature:: Multi-step reaction with 5 steps

1: 65 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.25 h

2: 91 percent / 4-dimethylaminopyridine / toluene / 3 h / Heating

3: 91 percent / AIBN; (n-Bu)3SnH / toluene / 0.08 h / Heating

4: KOH / methanol; H₂O / 2 h / 20 °C

5: oxalyl chloride; N,N-dimethylformamide / CH₂Cl₂ / 1 h

With dmap; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; N,N-dimethyl-formamide; In methanol; dichloromethane; water; toluene; 1: Luche reduction;
DOI:10.1021/jo049724+

Reference yield:

: [(1R,5R,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester

: 1054655-93-4
[(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride

Guidance literature:: Multi-step reaction with 2 steps

1: Bu₃SnH; AIBN / 0.17 h / Heating

2: aq. NaOH; oxalyl chloride / CH₂Cl₂ / 20 °C

With sodium hydroxide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; 1: Reduction / 2: 15;
DOI:10.1021/ol0056271