(3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-4-carboxylic acid benzyl ester

Base Information

Chemical Name:(3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-4-carboxylic acid benzyl ester
CAS No.:226915-57-7
Molecular Formula:C₂₁H₂₄O₄
Molecular Weight:340.419
Hs Code.:

Synonyms:(3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-4-carboxylic acid benzyl ester

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Chemical Property of (3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-4-carboxylic acid benzyl ester

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Technology Process of (3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-4-carboxylic acid benzyl ester

There total 6 articles about (3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-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: 66.0%

: 226915-55-5
(2R)-4-(3-cyclohex-1-enylacryloyloxy)pent-2-ynoic acid benzyl ester

: 226915-57-7
(3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-4-carboxylic acid benzyl ester

Guidance literature:: (2R)-4-(3-cyclohex-1-enylacryloyloxy)pent-2-ynoic acid benzyl ester; With hydrogen; triethylamine; Lindlar's catalyst; In tetrahydrofuran; for 16h;

In o-xylene; at 210 ℃; for 6h; In a pressure tube;

Reference yield: 66.0%

: 866888-52-0
(Z)-(R)-4-((E)-3-Cyclohex-1-enyl-acryloyloxy)-pent-2-enoic acid benzyl ester

: 226915-57-7
(3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-4-carboxylic acid benzyl ester

Guidance literature:: (Z)-(R)-4-((E)-3-Cyclohex-1-enyl-acryloyloxy)-pent-2-enoic acid benzyl ester; In xylene; at 210 ℃; for 6h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In xylene; at 20 ℃; for 0.5h;
DOI:10.1021/jm0502236

Reference yield:

: 226915-53-3
(2R)-4-hydroxypentyl-2-ynoic acid benzyl ester

: 226915-57-7
(3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydronaphtho[2,3-c]furan-4-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 63 percent / DCC; 4-pyrrolidinylpyridine / CH₂Cl₂

2: H₂; TEA / Lindlar catalyst / tetrahydrofuran

3: xylene / 185 °C

4: DBU / tetrahydrofuran

With TEA; hydrogen; 4-pyrrolidin-1-ylpyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; xylene; 3: Diels-Alder reaction;
DOI:10.1016/j.bmcl.2005.12.042