(3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

Base Information

Chemical Name:(3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester
CAS No.:359675-50-6
Molecular Formula:C₂₅H₃₃NO₇
Molecular Weight:459.54
Hs Code.:

(3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

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Chemical Property of (3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

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Technology Process of (3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

There total 13 articles about (3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl 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:

: 359436-42-3
(3aS,3bR,6S,6aS,7aR)-6-(3-Methoxycarbonyl-2-oxo-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

: 359675-50-6
(3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

Guidance literature:: With zinc(II) tetrahydroborate; In diethyl ether; at 0 ℃;
DOI:10.1016/S0040-4039(01)00782-1

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 359675-50-6
(3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: K₂CO₃ / diethyl ether

2.1: 71 percent / NaH; NaI / tetrahydrofuran

3.1: Ph₂O / 280 °C

4.1: BH₃*Me₂S / tetrahydrofuran / 0 °C

4.2: 89 percent / H₂O₂; NaOH; water

5.1: 90 percent / PCC / CH₂Cl₂

6.1: 81 percent / LiHMDS / tetrahydrofuran / -78 °C

7.1: Zn(BH₄)2 / diethyl ether / 0 °C

With zinc(II) tetrahydroborate; diphenylether; dimethylsulfide borane complex; sodium hydride; potassium carbonate; pyridinium chlorochromate; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(01)00782-1

Reference yield:

: 133693-88-6
(2-chloroethylidene)cyclopentane

: 359675-50-6
(3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 75 percent / NaH; NaI / tetrahydrofuran

2.1: 95 percent / TBAF / tetrahydrofuran

3.1: 98 percent / NaH / tetrahydrofuran / -30 - 0 °C

4.1: Ph₂O / 280 °C

5.1: BH₃*Me₂S / tetrahydrofuran / 0 °C

5.2: 89 percent / H₂O₂; NaOH; water

6.1: 90 percent / PCC / CH₂Cl₂

7.1: 81 percent / LiHMDS / tetrahydrofuran / -78 °C

8.1: Zn(BH₄)2 / diethyl ether / 0 °C

With zinc(II) tetrahydroborate; diphenylether; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium hydride; pyridinium chlorochromate; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4039(01)00782-1