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

Base Information

• Chemical Name: 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
• CAS No.: 1338566-17-8
• Molecular Formula: C₃₈H₅₀O₈SSi
• Molecular Weight: 694.962
• Mol file: 1338566-17-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 81.0%

3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)prop-1-en-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 (1338566-17-8)

Guidance literature:

With tert.-butylhydroperoxide; potassium tert-butylate; In tetrahydrofuran; at -78 - -25 ℃; Inert atmosphere;

DOI:10.1021/jo302267f

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

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:

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

(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:

C₅₃H₇₈O₁₂SSi₂

C₄₇H₇₃BrO₁₀Si₂

C₅₄H₇₄O₁₃SSi

(2R,4aR,5aS,7aR,8aS,12aR,13aS,14aR,15aS)-2-(((2S,3R,4aS,5aR,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexahydropyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin-3(2H)-one