(2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol

Base Information

Chemical Name:(2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol
CAS No.:876288-72-1
Molecular Formula:C₄₀H₄₈Br₂O₅Si
Molecular Weight:796.712
Hs Code.:

Synonyms:(2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol

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Chemical Property of (2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol

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Technology Process of (2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol

There total 4 articles about (2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol 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: 88.0%

: 876288-71-0
(2'R,3'S,5'R,7'S,8'R)-7'-(4-bromobenzyloxy)-8'-(4-bromobenzyloxymethyl)-2'-(tret-butyldimethylsilyloxymethyl)-5'-methyl-oxocan-3'-yl 2,2-dimethylpropionate

: 876288-72-1
(2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1016/j.tetlet.2005.11.085

Reference yield:

: 876288-69-6
(1'R,3'S,4'R,6'R,8'S,10'R)-3'-(tret-butyldimethylsilyloxymethyl)-6'-methyl-10'-phenyl-2',9',11'-trioxabicyclo[6.4.0]dodecan-4'-yl 2,2-dimethylpropionate

: 876288-72-1
(2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / 1,2-ethanedithiol; NaHCO₃; Zn(OTf)2 / CH₂Cl₂ / 5 h / 0 - 25 °C

2: 100 percent / TBAI; NaH / tetrahydrofuran / 16 h / 0 - 25 °C

3: 88 percent / diisobutyl aluminium hydride / CH₂Cl₂; hexane / 2 h / -78 °C

With tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ethane-1,2-dithiol; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.tet.2006.05.014

Reference yield:

: 475641-60-2
(2R,4aR,6S,7R,9S,10aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

: 876288-72-1
(2S,3R,5S,7S,8R)-7-(4-bromobenzyloxy)-8-(4-bromobenzyloxymethyl)-2-(tret-butyldimethylsilyloxymethyl)-5-methyl-oxocan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / pyridine / 14 h / 0 - 26 °C

2: 100 percent / 1,2-ethanedithiol; NaHCO₃; Zn(OTf)2 / CH₂Cl₂ / 5 h / 0 - 25 °C

3: 100 percent / TBAI; NaH / tetrahydrofuran / 16 h / 0 - 25 °C

4: 88 percent / diisobutyl aluminium hydride / CH₂Cl₂; hexane / 2 h / -78 °C

With pyridine; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ethane-1,2-dithiol; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.tet.2006.05.014