(1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol

Base Information

Chemical Name:(1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol
CAS No.:851129-90-3
Molecular Formula:C₂₁H₃₂O₅SSi
Molecular Weight:424.634
Hs Code.:

Synonyms:(1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol

Suppliers and Price of (1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol

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 (1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol

There total 8 articles about (1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol 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: 52.0%

: 851129-88-9
(1S,2R,3R,4S)-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-5-ene-1,4-diol

: 69739-34-0
t-butyldimethylsiyl triflate

: 851129-90-3
(1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol050287a

Reference yield:

: 851129-82-3
(4R,5R)-6-Bromo-4-hydroxy-5-methyl-4-((R)-toluene-4-sulfinylmethyl)-cyclohex-2-enone

: 851129-90-3
(1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1: Li₂CO₃; LiBr / dimethylformamide / 100 °C

2: 99 percent / meta-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

3: 72 percent / benzyltrimethylammonium hydroxide; tert-butyl hydroperoxide / methanol; tetrahydrofuran / 0 °C

4: 67 percent / DIBALH / tetrahydrofuran; hexane / 0.5 h / -78 °C

5: 52 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; N-benzyl-trimethylammonium hydroxide; lithium carbonate; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200601330

Reference yield:

: 851129-86-7
(2S,3R,4S)-2,3-epoxy-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1-one

: 851129-90-3
(1S,2S,3R,4S)-4-[(tert-butyldimethylsiloxy)oxy]-2,3-epoxy-6-methyl-1-[(p-tolylsulfonyl)methyl]-5-cyclohexen-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 67 percent / DIBALH / tetrahydrofuran; hexane / 0.5 h / -78 °C

2: 52 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/chem.200601330