Tert-butyl-dimethyl-[[(1R,2R,4R,6R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-yl]oxy]silane

Base Information

• Chemical Name: Tert-butyl-dimethyl-[[(1R,2R,4R,6R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-yl]oxy]silane
• CAS No.: 121289-19-8
• Molecular Formula: C16H30O2Si
• Molecular Weight: 282.49400
• DSSTox Substance ID: DTXSID20463118
• Nikkaji Number: J1.944.090G
• Wikidata: Q82287903
• Mol file: 121289-19-8.mol

Synonyms:Tert-butyl-dimethyl-[[(1R,2R,4R,6R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-yl]oxy]silane;121289-19-8;SCHEMBL4330072;DTXSID20463118

Chemical Property of Tert-butyl-dimethyl-[[(1R,2R,4R,6R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-yl]oxy]silane

Chemical Property:

• PSA: 21.76000
• LogP: 4.52040
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 282.201506730
• Heavy Atom Count: 19
• Complexity: 383

Purity/Quality:

97% ^*data from raw suppliers

6-tert-Butyldimethylsilyloxy-4-(1-methylethenyl)-1-methyl-cyclohexane1,2-Epoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=C)C1CC2C(O2)(C(C1)O[Si](C)(C)C(C)(C)C)C
• Isomeric SMILES: CC(=C)[C@@H]1C[C@@H]2[C@@](O2)([C@@H](C1)O[Si](C)(C)C(C)(C)C)C
• Uses: Intermediate in the preparation of Dihydroxyvitamin D3 and associated metabolites.

Technology Process of Tert-butyl-dimethyl-[[(1R,2R,4R,6R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-yl]oxy]silane

There total 4 articles about Tert-butyl-dimethyl-[[(1R,2R,4R,6R)-1-methyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-yl]oxy]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: 98.0%

(1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol (35692-59-2) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl-[(1S,2S,4R,6R)-4-iso-propenyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yloxy]dimethylsilane (121289-19-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1021/jo00276a003

Reference yield:

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (36616-60-1) → tert-butyl-[(1S,2S,4R,6R)-4-iso-propenyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yloxy]dimethylsilane (121289-19-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / L-Selectride / tetrahydrofuran

2: 94 percent / imidazole / toluene; dimethylformamide / 20 °C

With 1H-imidazole; L-Selectride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-2003-41025

Reference yield:

(R)-Carvone (6485-40-1,2244-16-8) → tert-butyl-[(1S,2S,4R,6R)-4-iso-propenyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yloxy]dimethylsilane (121289-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂O₂; NaOH / methanol

2: 85 percent / L-Selectride / tetrahydrofuran

3: 94 percent / imidazole / toluene; dimethylformamide / 20 °C

With 1H-imidazole; sodium hydroxide; dihydrogen peroxide; L-Selectride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1055/s-2003-41025

upstream raw materials:

(1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol

tert-butyldimethylsilyl chloride

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one

(R)-Carvone

Downstream raw materials:

(1S,2S,4R,6R)-2,4-bis(tert-butyldimethylsilyloxy)-1-methyl-7-oxabicyclo[4.1.0]heptane

(1R,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

(1S,2R,3R,5S)-3-benzyloxy-5-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

(1S,3R,5R)-3-benzyloxy-1,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexane