(Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

Base Information

• Chemical Name: (Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone
• CAS No.: 1338565-58-4
• Molecular Formula: C₂₀H₃₂O₄SSi
• Molecular Weight: 396.623
• Mol file: 1338565-58-4.mol

Synonyms:(Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

Chemical Property of (Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone

There total 2 articles about (Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone 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: 68.0%

(phenylsulfonylmethyl)trimethylsilane (17872-92-3) + 2-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)acetaldehyde (125878-02-6) → (Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone (1338565-58-4) + (E)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone (1338565-59-5)

Guidance literature:

(phenylsulfonylmethyl)trimethylsilane; With n-butyllithium; In 1,2-dimethoxyethane; hexane; at -80 ℃; for 0.5h; Inert atmosphere;

2-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)acetaldehyde; In 1,2-dimethoxyethane; hexane; at -80 ℃; for 0.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol202467z

Reference yield:

tert-Butyl-((2R,3S)-2-[1,3]dithian-2-ylmethyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane (441351-08-2) → (Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone (1338565-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: mercury(II) perchlorate; calcium carbonate / tetrahydrofuran; water / 2 h / 20 °C

2.1: n-butyllithium / 1,2-dimethoxyethane; hexane / 0.5 h / -80 °C / Inert atmosphere

2.2: 0.5 h / -80 °C / Inert atmosphere

With n-butyllithium; mercury(II) perchlorate; calcium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water;

DOI:10.1021/ol202467z

Reference yield:

(Z)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)prop-1-en-1-yl phenyl sulfone (1338565-58-4) → 3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone (1338566-17-8) + 3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone (1338566-17-8)

Guidance literature:

With tert.-butylhydroperoxide; potassium tert-butylate; In tetrahydrofuran; 2,2'-oxybis(2-methyl-propane); at -80 - -25 ℃; for 21h; optical yield given as %de;

DOI:10.1021/ol202467z

upstream raw materials:

(phenylsulfonylmethyl)trimethylsilane

2-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)acetaldehyde

tert-Butyl-((2R,3S)-2-[1,3]dithian-2-ylmethyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane

Downstream raw materials:

3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone

3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone

(1S,2R)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone

(1R,2S)-3-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone