(-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one

Base Information

Chemical Name:(-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one
CAS No.:292850-60-3
Molecular Formula:C₁₇H₂₁NO₅
Molecular Weight:319.357
Hs Code.:

Synonyms:(-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one

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Chemical Property of (-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one

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Technology Process of (-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one

There total 8 articles about (-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-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: 73.0%

: (2R,3aR,4R)-5-(4-methoxybenzyloxy)-pent-2-enoic acid 2-ethoxycarbonyl-2,3,3a,4,5,6-hexahydro-pyrrolo[1,2-b]isoxazol-4-yl ester

: 292850-60-3
(-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one

Guidance literature:: In 1,2-dichloro-benzene; at 150 ℃; for 3h;
DOI:10.1021/ol006125q

Reference yield: 71.0%

: 292850-58-9
(3aR,4R)-5-(4-methoxybenzyloxy)-pent-2-enoic acid 2-phenyl-2,3,3a,4,5,6-hexahydro-pyrrolo[1,2-b]isoxazol-4-yl ester

: 292850-60-3
(-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one

Guidance literature:: In 1,2-dichloro-benzene; at 190 ℃; for 64h;
DOI:10.1021/ol006125q

Reference yield:

: 123-11-5
4-methoxy-benzaldehyde

: 292850-60-3
(-)-(2aR,3S,6aR,6bR)-hexahydro-3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / pTsOH*H₂O / toluene / 11 h / 110 °C

2: 91 percent / DIBAL / toluene / 20 °C

3: DMSO; oxalyl chloride; TEA / CH₂Cl₂

4: 98 percent / K₂CO₃ / H₂O / 20 °C

5: 72 percent / NaOH / tetrahydrofuran; H₂O / 5 h / 20 °C

With sodium hydroxide; oxalyl dichloride; TEA; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; toluene; 3: Swern oxidation / 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/1099-0690(200206)2002:12<1941::AID-EJOC1941>3.0.CO;2-T