(3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester
• CAS No.: 359436-43-4
• Molecular Formula: C₂₅H₃₁NO₆
• Molecular Weight: 441.524

Synonyms:(3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

Chemical Property of (3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

There total 14 articles about (3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-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:

(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 (359675-50-6) → (3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester (359436-43-4)

Guidance literature:

(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; With methanesulfonyl chloride; triethylamine; In dichloromethane;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(01)00782-1

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester (359436-43-4)

Guidance literature:

Multi-step reaction with 8 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

8.1: MsCl; Et₃N / CH₂Cl₂

8.2: DBU / tetrahydrofuran / Heating

With zinc(II) tetrahydroborate; diphenylether; dimethylsulfide borane complex; sodium hydride; potassium carbonate; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(01)00782-1

Reference yield:

(2-chloroethylidene)cyclopentane (133693-88-6) → (3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester (359436-43-4)

Guidance literature:

Multi-step reaction with 9 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

9.1: MsCl; Et₃N / CH₂Cl₂

9.2: DBU / tetrahydrofuran / Heating

With zinc(II) tetrahydroborate; diphenylether; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium hydride; methanesulfonyl chloride; triethylamine; pyridinium chlorochromate; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(01)00782-1

upstream raw materials:

(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

benzyl chloroformate

(2-chloroethylidene)cyclopentane

[(3aS,4R,6S,6aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-carbamic acid benzyl ester

Downstream raw materials:

(3S,3aS,5R,6S,6aR)-5,6-Dihydroxy-3-(6-methoxycarbonyl-pyridin-3-yl)-hexahydro-cyclopenta[b]pyrrole-1-carboxylic acid benzyl ester

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