(1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene

Base Information

Chemical Name:(1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene
CAS No.:765950-80-9
Molecular Formula:C₃₅H₄₁ClO₄
Molecular Weight:561.161
Hs Code.:

(1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene

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Chemical Property of (1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene

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Technology Process of (1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene

There total 18 articles about (1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene 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:

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

: 765950-80-9
(1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene

Guidance literature:: Multi-step reaction with 10 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: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C

8.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 25 °C

9.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C

9.2: 77 percent / pentane; diethyl ether / 2.5 h / -78 - 0 °C

10.1: 73 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 0.5 h / 25 °C

With 1H-imidazole; lead(IV) acetate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; Dess-Martin periodane; methanesulfonyl chloride; (+)-10-camphorsulfonic acid; 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

: 765950-80-9
(1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene

Guidance literature:: Multi-step reaction with 11 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: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 36 h / 25 °C

9.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 25 °C

10.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C

10.2: 77 percent / pentane; diethyl ether / 2.5 h / -78 - 0 °C

11.1: 73 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 0.5 h / 25 °C

With 1H-imidazole; lead(IV) acetate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; tert.-butyl lithium; Dess-Martin periodane; methanesulfonyl chloride; (+)-10-camphorsulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; benzene;
DOI:10.1021/jo0491399

Reference yield:

: 765950-74-1
formic acid 3,4-bis-benzyloxy-5-chloro-phenyl ester

: 765950-80-9
(1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene

Guidance literature:: Multi-step reaction with 5 steps

1.1: K₂CO₃ / methanol / 1 h / 0 °C

2.1: 1.49 g / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 h / 25 °C

3.1: 96 percent / N-bromosuccinimide / CH₂Cl₂ / 8 h / 25 °C

4.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C

4.2: 77 percent / pentane; diethyl ether / 2.5 h / -78 - 0 °C

5.1: 73 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 0.5 h / 25 °C

With dmap; N-Bromosuccinimide; tert.-butyl lithium; potassium carbonate; (+)-10-camphorsulfonic acid; triethylamine; In methanol; diethyl ether; dichloromethane; pentane;
DOI:10.1021/jo0491399