(1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide

Base Information

Chemical Name:(1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide
CAS No.:264218-65-7
Molecular Formula:C₃₃H₄₄N₂O₅
Molecular Weight:548.723
Hs Code.:

Synonyms:(1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide

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Chemical Property of (1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide

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Technology Process of (1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide

There total 8 articles about (1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide 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: 82.0%

: 59578-63-1
4-(benzylamino)-1-butanol

: 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

: 264218-65-7
(1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide

Guidance literature:: With sodium hydroxide; In dichloromethane; for 1.5h;
DOI:10.1021/jo049724+

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

: 264218-65-7
(1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide

Guidance literature:: Multi-step reaction with 6 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

6: 82 percent / NaOH / CH₂Cl₂ / 1.5 h

With dmap; potassium hydroxide; sodium 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

: 264218-65-7
(1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: Bu₃SnH; AIBN / 0.17 h / Heating

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

3: 82 percent

With sodium hydroxide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; 1: Reduction / 2: 15 / 3: Substitution;
DOI:10.1021/ol0056271