(3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester
• CAS No.: 391677-13-7
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• Mol file: 391677-13-7.mol

Synonyms:(3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester

Chemical Property of (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester

There total 14 articles about (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-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: 83.0%

(3R,3aS,5S,7aR)-7-Hydroxy-3-isopropenyl-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester → (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester (391677-13-7)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(01)01558-1

Reference yield:

(1R,3R,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-ol → (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester (391677-13-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Et₃N / CH₂Cl₂

2.1: sodium azide / dimethylformamide / 80 °C

2.2: imidazole

3.1: LiAlH₄ / diethyl ether / 0 °C

4.1: K₂CO₃ / 0 °C

5.1: 83 percent / NaH / dimethylformamide / 0 °C

6.1: 98 percent / sodium hydrogen carbonate / diphenyl ether / 0.5 h / Heating

7.1: 97 percent / TBAF / tetrahydrofuran

8.1: Et₃N / CH₂Cl₂

9.1: LiI / tetrahydrofuran / Heating

10.1: 90 percent / zinc / methanol; acetic acid / Heating

11.1: 83 percent / TPAP-NMO / CH₂Cl₂; acetonitrile

With lithium aluminium tetrahydride; sodium azide; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; lithium iodide; zinc; In tetrahydrofuran; methanol; diphenylether; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(01)01558-1

Reference yield:

(1R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one → (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester (391677-13-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -78 °C

2.1: Et₃N / CH₂Cl₂

3.1: sodium azide / dimethylformamide / 80 °C

3.2: imidazole

4.1: LiAlH₄ / diethyl ether / 0 °C

5.1: K₂CO₃ / 0 °C

6.1: 83 percent / NaH / dimethylformamide / 0 °C

7.1: 98 percent / sodium hydrogen carbonate / diphenyl ether / 0.5 h / Heating

8.1: 97 percent / TBAF / tetrahydrofuran

9.1: Et₃N / CH₂Cl₂

10.1: LiI / tetrahydrofuran / Heating

11.1: 90 percent / zinc / methanol; acetic acid / Heating

12.1: 83 percent / TPAP-NMO / CH₂Cl₂; acetonitrile

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; cerium(III) chloride; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; lithium iodide; zinc; In tetrahydrofuran; methanol; diphenylether; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(01)01558-1

upstream raw materials:

benzyl chloroformate

Downstream raw materials:

(2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester