(4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

Base Information

Chemical Name:(4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one
CAS No.:349552-43-8
Molecular Formula:C₁₉H₂₄O₄
Molecular Weight:316.397
Hs Code.:

Synonyms:(4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

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Chemical Property of (4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

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Technology Process of (4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

There total 10 articles about (4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-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: 85.0%

: 349552-44-9
(4aS,6S,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

: 349552-43-8
(4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene-d6; at 25 ℃; for 79h;
DOI:10.1055/s-2001-13387

Reference yield: 47.0%

: 349552-42-7
(4aS,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,6,7,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-7-ol

: 349552-43-8
(4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

: 349552-44-9
(4aS,6S,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

Guidance literature:: In dichloromethane; at 20 ℃; for 3h;
DOI:10.1055/s-2001-13387

Reference yield:

: 175664-06-9
(2R,3S)-2-(2',2'-dibromovinyl)-3-(tert-butyldimethylsiloxy)-tetrahydropyran

: 349552-43-8
(4aS,6R,9aR)-6-(3-Benzyloxy-propyl)-3,4,4a,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-7-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: 89 percent / BuLi / tetrahydrofuran / 4 h / -78 - 0 °C

2.1: H₂; quinoline / Lindlar catalyst / ethanol / 28 h / 20 °C

3.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 0.75 h / -78 - 20 °C

4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

4.2: 85 percent / tetrahydrofuran / 1.5 h / -78 °C

5.1: 100 percent / TBAF / tetrahydrofuran / 5 h / 20 °C

6.1: TFA / H₂O; tetrahydrofuran / 2 h / 20 °C

7.1: Et₃SiH; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

8.1: 47 percent / CH₂Cl₂ / 3 h / 20 °C

With quinoline; triethylsilane; n-butyllithium; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; water; 3.1: Swern oxidation / 8.1: Dess-Martin periodinane;
DOI:10.1055/s-2001-13387