(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene

Base Information

• Chemical Name: (3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene
• CAS No.: 116506-66-2
• Molecular Formula: C₂₁H₄₀Br₂O₂Si₂
• Molecular Weight: 540.526
• Mol file: 116506-66-2.mol

Synonyms:(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene

Chemical Property of (3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene

There total 8 articles about (3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene 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:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → (3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene (116506-66-2)

Guidance literature:

Multi-step reaction with 8 steps

2: 86 percent / tert-butylhydroperoxide, / vanadyl acetyl acetonate / benzene; toluene / 3 h / Ambient temperature

3: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature

4: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8

5: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h

6: 90 percent / sodium methoxide / methanol / 5 h / Ambient temperature

7: 90 percent / imidazole / CH₂Cl₂ / 10 h / Ambient temperature

8: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; osmium(VIII) oxide; potassium metaperiodate; oxalyl dichloride; sodium methylate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; toluene; benzene;

DOI:10.1016/S0040-4020(01)86410-3

Reference yield:

(1R,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-methanol (4895-08-3) → (3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene (116506-66-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / tert-butylhydroperoxide, / vanadyl acetyl acetonate / benzene; toluene / 3 h / Ambient temperature

2: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature

3: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8

4: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h

5: 90 percent / sodium methoxide / methanol / 5 h / Ambient temperature

6: 90 percent / imidazole / CH₂Cl₂ / 10 h / Ambient temperature

7: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; osmium(VIII) oxide; potassium metaperiodate; oxalyl dichloride; sodium methylate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; toluene; benzene;

DOI:10.1016/S0040-4020(01)86410-3

Reference yield:

(3S,5R)-3,5-Dihydroxy-2-methyl-cyclohex-1-enecarbaldehyde (75212-02-1) → (3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene (116506-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / imidazole / CH₂Cl₂ / 10 h / Ambient temperature

2: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.

With pyridine; 1H-imidazole; triphenylphosphine; zinc; In dichloromethane;

DOI:10.1016/S0040-4020(01)86410-3

upstream raw materials:

carbon tetrabromide

3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enecarbaldehyde

(S)-p-mentha-6,8-dien-2-one

(1R,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-methanol

Downstream raw materials:

TB

calcitriol

1α-Hydroxy-25-oxo-27-norvitamin D₃

1α-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norprevitamin D₃ tert-butyldimethylsilyl ether