(1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester
• CAS No.: 95531-83-2
• Molecular Formula: C₃₃H₅₂O₅Si
• Molecular Weight: 556.858
• Mol file: 95531-83-2.mol

Synonyms:(1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester

Chemical Property of (1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester

There total 8 articles about (1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-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: 86.0%

(1S,4aS,8aR)-3-((E)-5-Benzyloxy-2-methyl-pent-2-enyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carboxylic acid methyl ester (95531-82-1) → (1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester (95531-83-2)

Guidance literature:

In nonane; for 36h; Heating;

DOI:10.1021/ja00295a027

Reference yield:

(4R,4aR,8aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-4a-methyl-octahydro-naphthalen-2-one (95532-02-8) → (1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester (95531-83-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium herxamethyldisilazide / tetrahydrofuran / 1.) 0 degC, 7 h; 2.) -78 degC, 1 h

2: 89 percent / potassium tert-butoxide, sodium iodide / hexamethylphosphoric acid triamide / 6 h / 60 °C

3: 86 percent / nonane / 36 h / Heating

With potassium tert-butylate; sodium hexamethyldisilazane; sodium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; nonane;

DOI:10.1021/ja00295a027

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1S,2S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester (95531-83-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 25 °C

2: 1.) sodium herxamethyldisilazide / tetrahydrofuran / 1.) 0 degC, 7 h; 2.) -78 degC, 1 h

3: 89 percent / potassium tert-butoxide, sodium iodide / hexamethylphosphoric acid triamide / 6 h / 60 °C

4: 86 percent / nonane / 36 h / Heating

With dmap; potassium tert-butylate; sodium hexamethyldisilazane; triethylamine; sodium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; nonane; dichloromethane;

DOI:10.1021/ja00295a027

upstream raw materials:

(1S,4aS,8aR)-3-((E)-5-Benzyloxy-2-methyl-pent-2-enyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-8a-methyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carboxylic acid methyl ester

(4R,4aR,8aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-4a-methyl-octahydro-naphthalen-2-one

tert-butyldimethylsilyl chloride

(1R,2R,4aS,8aR)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester

Downstream raw materials:

(1S,2S,3R,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-8a-methyl-decahydro-naphthalene-2-carboxylic acid methyl ester

(1S,2S,3S,4aS,8aR)-2-[(R)-1-(2-Benzyloxy-ethyl)-2-methyl-allyl]-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-8a-methyl-decahydro-naphthalene-2-carboxylic acid methyl ester

(1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol

C₂₆H₃₈O₅