(2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

Base Information

Chemical Name:(2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one
CAS No.:370884-48-3
Molecular Formula:C₁₅H₁₈O₄
Molecular Weight:262.306
Hs Code.:

Synonyms:(2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

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Chemical Property of (2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

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Technology Process of (2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

There total 5 articles about (2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-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: 98.0%

: 730240-89-8
4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid

: 370884-48-3
(2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

Guidance literature:: 4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃;

With dmap; In benzene; at 20 ℃;
DOI:10.1016/S0040-4039(01)01205-9

Reference yield:

: 250226-93-8
(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester

: 370884-48-3
(2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / H₂ / 5 percent Pd/C / ethyl acetate / 10 h / 20 °C

2.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

4.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

5.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

With lithium hydroxide; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; 2.1: Swern oxidation / 5.1: Yamaguchi lactonization;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 116237-17-3
4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

: 370884-48-3
(2R,4aR,9aS)-4a-Methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

1.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

3.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

4.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

4.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

With lithium hydroxide; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; 1.1: Swern oxidation / 4.1: Yamaguchi lactonization;
DOI:10.1016/S0040-4020(02)00039-X