(1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

Base Information

Chemical Name:(1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane
CAS No.:498554-05-5
Molecular Formula:C₂₆H₄₄O₅Si₂
Molecular Weight:492.803
Hs Code.:

Synonyms:(1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

Suppliers and Price of (1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

There total 2 articles about (1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane 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%

: 75-24-1
trimethylaluminum

: 498554-04-4
4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone

: 498554-05-5
(1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

Guidance literature:: trimethylaluminum; With titanocene dichloride; In toluene; at 23 ℃; for 72h;

4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone; In tetrahydrofuran; toluene; at 0 - 24 ℃;
DOI:10.1016/S0040-4020(02)01329-7

Reference yield:

: 113533-88-3,113533-89-4
4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucopyranose

: 498554-05-5
(1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: titanocene dichloride / toluene / 72 h / 23 °C

2.2: 100 percent / toluene; tetrahydrofuran / 0 - 24 °C

With oxalyl dichloride; titanocene dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 1.1: Swern oxidation / 2.2: Tebbe olefination;
DOI:10.1016/S0040-4020(02)01329-7

Reference yield: 80.0%

: 498554-05-5
(1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane

: {(1R,3R,6R,9S,10S)-9,10-bis(tert-butyldimethylsilyloxy)-3-phenyl-2,4,7-trioxabicyclo[4.4.0]dec-8-yl}methanol

Guidance literature:: (1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane; With borane-THF; In tetrahydrofuran; at 0 ℃; for 4.5h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 24 ℃; for 1.5h;
DOI:10.1016/S0040-4020(02)01329-7