(1R^*,3R^*,7S^*,8S^*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphoxide-2,4-dioxatricyclo<6.2.1.0^3,7>undecane

Base Information

• Chemical Name: (1R^*,3R^*,7S^*,8S^*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphoxide-2,4-dioxatricyclo<6.2.1.0^3,7>undecane
• CAS No.: 111917-83-0
• Molecular Formula: C₂₁H₃₂O₄SSi
• Molecular Weight: 408.634
• Mol file: 111917-83-0.mol

Synonyms:

Chemical Property of (1R^*,3R^*,7S^*,8S^*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphoxide-2,4-dioxatricyclo<6.2.1.0^3,7>undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R^*,3R^*,7S^*,8S^*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphoxide-2,4-dioxatricyclo<6.2.1.0^3,7>undecane

There total 9 articles about (1R^*,3R^*,7S^*,8S^*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphoxide-2,4-dioxatricyclo<6.2.1.0^3,7>undecane 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: 83.0%

(1R*,3R*,7S*,8S*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphide-2,4-dioxatricyclo<6.2.1.03,7>undecane (111917-82-9,138051-93-1,138052-02-5) → (1R*,3R*,7S*,8S*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphoxide-2,4-dioxatricyclo<6.2.1.03,7>undecane (111917-83-0,138051-94-2,138052-03-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/S0040-4039(00)95691-0

Reference yield:

(1R*,3S*,7S*,8S*)-7-(tert-Butyldimethylsilyloxy)-2,4-dioxatricyclo<6.2.1.03,7>undecan-5-ol (111917-81-8,138051-92-0,138052-01-4) → (1R*,3R*,7S*,8S*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphoxide-2,4-dioxatricyclo<6.2.1.03,7>undecane (111917-83-0,138051-94-2,138052-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Amberlyst 15, 4 Angstroem molecular sieves / acetonitrile / 0.5 h / Ambient temperature

2: 72 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

With Amberlyst 15; 4 A molecular sieve; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)82332-2

Reference yield:

(1R*,3S*,7R*,8S*)-7-Hydroxy-2,4-dioxatricyclo<6.2.1.03,7>undec-5-ene (111917-73-8,138124-91-1) → (1R*,3R*,7S*,8S*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphoxide-2,4-dioxatricyclo<6.2.1.03,7>undecane (111917-83-0,138051-94-2,138052-03-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) O₃, 2) triphenylphosphine / 1) CH₂Cl₂, -78 deg C, 2) 2 h, room temp.

2: 82 percent / 4 Angstroem sieves / Amberlyst 15 / acetonitrile

3: 83 percent / m-chloroperbenzoic acid / CH₂Cl₂

With 4 A molecular sieve; ozone; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; Amberlyst 15; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)95691-0

upstream raw materials:

(1R^*,3R^*,7S^*,8S^*)-7-(tert-Butyldimethylsilyloxy)-5-phenylsulphide-2,4-dioxatricyclo<6.2.1.0^3,7>undecane

2-oxabicyclo[3.2.1]octan-3-one

(1R^*,4R^*,5S^*)-4-Hydroxy-2-oxabicyclo<3.2.1>octan-3-one

(1R^*,3S^*,7S^*,8S^*)-7-(tert-Butyldimethylsilyloxy)-2,4-dioxatricyclo<6.2.1.0^3,7>undecan-5-ol