(1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.0^2,11]undec-7-en-3-ol

Base Information

• Chemical Name: (1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.0^2,11]undec-7-en-3-ol
• CAS No.: 210552-65-1
• Molecular Formula: C₃₄H₄₉O₄PSi
• Molecular Weight: 580.82

Synonyms:(1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.0^2,11]undec-7-en-3-ol

Chemical Property of (1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.0^2,11]undec-7-en-3-ol

Chemical Property:

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Technology Process of (1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.0^2,11]undec-7-en-3-ol

There total 4 articles about (1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.0^2,11]undec-7-en-3-ol 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:

tert-butyldimethylsilyl chloride (18162-48-6) → (1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.02,11]undec-7-en-3-ol (210552-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h

2: 86 percent / N-methylmorpholine N-oxide, 4 A molecular sieves, TPAP / CH₂Cl₂ / 3 h

3: 1.) LDA / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 30 min

With 1H-imidazole; tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/ja980691n

Reference yield:

(1R,2R,3S,4R,11S)-4-(2-Hydroxy-ethyl)-11-methyl-tricyclo[5.4.0.02,11]undec-7-en-3-ol → (1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.02,11]undec-7-en-3-ol (210552-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h

2: 86 percent / N-methylmorpholine N-oxide, 4 A molecular sieves, TPAP / CH₂Cl₂ / 3 h

3: 1.) LDA / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 30 min

With 1H-imidazole; tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/ja980691n

Reference yield:

(1R,2R,3S,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-11-methyl-tricyclo[5.4.0.02,11]undec-7-en-3-ol → (1R,2R,3R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-(diphenyl-phosphinoyl)-methoxy-methyl]-11-methyl-tricyclo[5.4.0.02,11]undec-7-en-3-ol (210552-65-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / N-methylmorpholine N-oxide, 4 A molecular sieves, TPAP / CH₂Cl₂ / 3 h

2: 1.) LDA / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 30 min

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/ja980691n

upstream raw materials:

(methoxymethyl)diphenylphosphine oxide

(1R,2R,4R,11S)-4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-11-methyl-tricyclo[5.4.0.0^2,11]undec-7-en-3-one

tert-butyldimethylsilyl chloride

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