(4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene

Base Information

Chemical Name:(4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene
CAS No.:765950-78-5
Molecular Formula:C₄₁H₄₃ClO₃Se
Molecular Weight:698.204
Hs Code.:

Synonyms:(4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene

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Chemical Property of (4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene

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Technology Process of (4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene

There total 20 articles about (4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene 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: 38.0%

: 682744-27-0
(1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-3H-2-methylene-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene

: 71098-88-9
N-phenylselanylphthalimide

: 765950-78-5
(4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene

: 682744-29-2
(4aS,6aS,12aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthen-12-ol

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -78 ℃; for 4h;
DOI:10.1021/jo0491399

Reference yield:

: 166406-74-2
(1S,3aR,5aS,9aS,9bR)-1-hydroxy-dodecahydro-3a,6,6,9a,-tetramethylnaphtho-[2,1-b]furan-2-one

: 765950-78-5
(4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene

Guidance literature:: Multi-step reaction with 11 steps

1.1: 30 percent / LiAlH₄ / tetrahydrofuran / 4 h / 25 °C

2.1: 91 percent / LiAlH₄ / tetrahydrofuran / 3 h

3.1: 90 percent / lead tetraacetate / benzene / 4 h / 25 °C

4.1: 97 percent / LiALH₄ / diethyl ether / 1 h / 20 °C

5.1: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C

6.1: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C

7.1: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 25 °C

8.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 25 °C

9.1: t-BuLi / pentane; diethyl ether / 0.5 h / -78 °C

9.2: 89 percent / pentane; diethyl ether / 2 h / -78 °C

10.1: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / 0 °C

11.1: 56 percent / SnCl₄ / CH₂Cl₂ / 4 h / -78 °C

With 1H-imidazole; lead(IV) acetate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tin(IV) chloride; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; benzene;
DOI:10.1021/jo0491399

Reference yield:

: 564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5
(3aR)-(+)-sclareolide

: 765950-78-5
(4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene

Guidance literature:: Multi-step reaction with 12 steps

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

1.2: 65.6 percent / MoO₅*pyridine*HMPA / tetrahydrofuran / 0.5 h / -78 °C

2.1: 30 percent / LiAlH₄ / tetrahydrofuran / 4 h / 25 °C

3.1: 91 percent / LiAlH₄ / tetrahydrofuran / 3 h

4.1: 90 percent / lead tetraacetate / benzene / 4 h / 25 °C

5.1: 97 percent / LiALH₄ / diethyl ether / 1 h / 20 °C

6.1: 98 percent / imidazole / dimethylformamide / 2 h / 25 °C

7.1: 45 percent / triethylamine; methanesulfonyl chloride / tetrahydrofuran / 4 h / 25 °C

8.1: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 25 °C

9.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 25 °C

10.1: t-BuLi / pentane; diethyl ether / 0.5 h / -78 °C

10.2: 89 percent / pentane; diethyl ether / 2 h / -78 °C

11.1: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / 0 °C

12.1: 56 percent / SnCl₄ / CH₂Cl₂ / 4 h / -78 °C

With 1H-imidazole; lead(IV) acetate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tin(IV) chloride; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; benzene;
DOI:10.1021/jo0491399