tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane
• CAS No.: 214351-86-7
• Molecular Formula: C₁₉H₃₇IOSi
• Molecular Weight: 436.492
• Mol file: 214351-86-7.mol

Synonyms:(1R,4S,7aR)-4-(tert-butyldimethylsilyloxy)octahydro-1-((R)-1-iodopropan-2-yl)-7a-methyl-1H-indene

Chemical Property of tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane

Chemical Property:

• Vapor Pressure: 5.12E-06mmHg at 25°C

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane

There total 9 articles about tert-Butyl-[1-(2-iodo-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-yloxy]-dimethyl-silane 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: 100.0%

(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(R)-2-hydroxy-1-methylethyl]-7a-methyl-1H-indene (171011-48-6,215509-33-4) → (1R,4S,7aR)-4-(tert-butyldimethylsilyloxy)octahydro-1-((R)-1-iodopropan-2-yl)-7a-methyl-1H-indene (214351-86-7)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 18.5h;

Reference yield: 94.0%

(R)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahyrdo-1H-inden-1-yl)propyl 4-methylbenzenesulfonate (183506-75-4) → (1R,4S,7aR)-4-(tert-butyldimethylsilyloxy)octahydro-1-((R)-1-iodopropan-2-yl)-7a-methyl-1H-indene (214351-86-7)

Guidance literature:

With sodium iodide; In N,N-dimethyl-formamide; at 20 - 85 ℃; Inert atmosphere;

DOI:10.3987/COM-09-11871

Reference yield:

(S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal (104651-47-0) → (1R,4S,7aR)-4-(tert-butyldimethylsilyloxy)octahydro-1-((R)-1-iodopropan-2-yl)-7a-methyl-1H-indene (214351-86-7)

Guidance literature:

Multi-step reaction with 4 steps

1: DBU / tetrahydrofuran / 12 h / Heating

2: 3.14 g / NaBH₄ / methanol / 1 h / 0 °C

3: 98 percent / pyridine / 13 h / 20 °C

4: 92 percent / NaI / dimethylformamide / 3 h / 85 °C

With pyridine; sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: epimerization / 2: Reduction / 3: Tosylation / 4: Substitution;

DOI:10.1016/S0968-0896(99)00262-X

upstream raw materials:

(R)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahyrdo-1H-inden-1-yl)propyl 4-methylbenzenesulfonate

(S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal

(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(R)-2-hydroxy-1-methylethyl]-7a-methyl-1H-indene

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

Downstream raw materials:

20-epi-25-hydroxyvitamin D₃

20-epi-vitamin D₃