(4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester
• CAS No.: 195527-11-8
• Molecular Formula: C₃₆H₅₈O₈Si₃
• Molecular Weight: 703.108
• Mol file: 195527-11-8.mol

Synonyms:(4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

Chemical Property of (4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

There total 3 articles about (4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl 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:

Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester (171925-86-3) → (4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester (195527-11-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / MeONa / H₂O / 17 h / Ambient temperature

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / Ambient temperature

3: 1.) LiHMDS, TMEDA / tetrahydrofuran / 1.) 0 deg C, 0.5 h, then room temp., 1.5 h; 2.) 0 deg C

With 2,6-dimethylpyridine; N,N,N,N,-tetramethylethylenediamine; sodium methylate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water;

DOI:10.1246/cl.1997.935

Reference yield:

(4aS,5S,6aR,7R,8S,10aS,10bR)-5,8-Dihydroxy-7-hydroxymethyl-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester (172704-62-0) → (4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester (195527-11-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / Ambient temperature

2: 1.) LiHMDS, TMEDA / tetrahydrofuran / 1.) 0 deg C, 0.5 h, then room temp., 1.5 h; 2.) 0 deg C

With 2,6-dimethylpyridine; N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1246/cl.1997.935

Reference yield:

benzoyl chloride (98-88-4) + (4aS,5S,6aR,7R,8S,10aS,10bR)-3,4a,7,10a-Tetramethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester (189564-01-0) → (4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester (195527-11-8)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; Yield given; 1.) 0 deg C, 0.5 h, then room temp., 1.5 h; 2.) 0 deg C;

DOI:10.1246/cl.1997.935

upstream raw materials:

benzoyl chloride

(4aS,5S,6aR,7R,8S,10aS,10bR)-3,4a,7,10a-Tetramethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

(4aS,5S,6aR,7R,8S,10aS,10bR)-5,8-Dihydroxy-7-hydroxymethyl-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

Downstream raw materials:

(3S,4R,4aR,6S,6aS,12aR,12bS)-4,6a,12b-Trimethyl-9-phenyl-3,6-bis-trimethylsilanyloxy-4-trimethylsilanyloxymethyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione

(3S,4R,4aR,6S,6aS,12aR,12bS)-3,6-Dihydroxy-4-hydroxymethyl-4,6a,12b-trimethyl-9-phenyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione

Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester