(1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene

Base Information

• Chemical Name: (1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene
• CAS No.: 125164-83-2
• Molecular Formula: C₁₈H₃₆O₄Si₂
• Molecular Weight: 372.652
• Mol file: 125164-83-2.mol

Synonyms:(1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene

Chemical Property of (1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene

There total 1 articles about (1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene 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: 45.0%

(5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-diene (125164-82-1) → (1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene (125164-83-2) + (1S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-2,5-dienyl-hydroperoxide (125164-84-3)

Guidance literature:

With oxygen; at -80 ℃; Irradiation;

DOI:10.1016/S0040-4039(00)99416-4

Reference yield:

(1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene (125164-83-2) → pinitol (10284-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1: thiourea / methanol

2: 95 percent / MCPBA

3: 60 percent / CF₃CO₂H / methanol

With thiourea; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol;

DOI:10.1016/S0040-4039(00)99416-4

Reference yield:

(1S,4R,7R,8S)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2,3-dioxa-bicyclo[2.2.2]oct-5-ene (125164-83-2) → (1S,4R,5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-ene-1,4-diol

Guidance literature:

With thiourea; In methanol;

DOI:10.1016/S0040-4039(00)99416-4

upstream raw materials:

(5S,6R)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-diene

Downstream raw materials:

pinitol