(Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal

Base Information

Chemical Name:(Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal
CAS No.:186819-77-2
Molecular Formula:C₂₄H₃₃NO₄
Molecular Weight:399.53
Hs Code.:

Synonyms:(Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal

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Chemical Property of (Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal

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Technology Process of (Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal

There total 13 articles about (Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal 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: 72.0%

: 186819-89-6
(5S,8S,8aR)-8-Benzyloxy-5-((Z)-10-hydroxy-dec-1-enyl)-hexahydro-oxazolo[3,4-a]pyridin-3-one

: 186819-77-2
(Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/jo961951r

Reference yield:

: 186819-83-0
(Z)-6-Methoxymethoxy-hex-4-en-1-ol

: 186819-77-2
(Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal

Guidance literature:: Multi-step reaction with 12 steps

1: 81 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

2: 88 percent / CH₂Cl₂

3: 94 percent / DIBALH / tetrahydrofuran

4: 80 percent / Ti(i-PrO)4, L-DIPT, t-BuOOH / CH₂Cl₂ / -23 °C

5: 2.) K₂CO₃, (C₈H₁₇)3NMeCl / 1.) THF, room temperature, 2.) MeCN

6: 72 percent / PdCl₂(CH₂CN)2 / tetrahydrofuran / Ambient temperature

7: 95 percent / aq. K₂CO₃ / methanol / Ambient temperature

8: 97 percent / NaH, Bu₄NI / tetrahydrofuran

9: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂

10: 65 percent / NaH, DMSO / tetrahydrofuran

11: 70 percent / aq. NaHCO₃ / methanol

12: 72 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; dimethylsulfide; L-(+)-diisopropyl tartrate; (C₈H₁₇)3NMeCl; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo961951r

Reference yield:

: 186819-71-6
6-Methoxymethoxy-hex-4-yn-1-ol

: 186819-77-2
(Z)-10-((5S,8S,8aR)-8-Benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-5-yl)-dec-9-enal

Guidance literature:: Multi-step reaction with 13 steps

1: 84 percent / H₂ / Lindlar catalyst / ethyl acetate

2: 81 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

3: 88 percent / CH₂Cl₂

4: 94 percent / DIBALH / tetrahydrofuran

5: 80 percent / Ti(i-PrO)4, L-DIPT, t-BuOOH / CH₂Cl₂ / -23 °C

6: 2.) K₂CO₃, (C₈H₁₇)3NMeCl / 1.) THF, room temperature, 2.) MeCN

7: 72 percent / PdCl₂(CH₂CN)2 / tetrahydrofuran / Ambient temperature

8: 95 percent / aq. K₂CO₃ / methanol / Ambient temperature

9: 97 percent / NaH, Bu₄NI / tetrahydrofuran

10: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂

11: 65 percent / NaH, DMSO / tetrahydrofuran

12: 70 percent / aq. NaHCO₃ / methanol

13: 72 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; dimethylsulfide; L-(+)-diisopropyl tartrate; (C₈H₁₇)3NMeCl; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; dichloro bis(acetonitrile) palladium(II); Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo961951r