(2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

Base Information

Chemical Name:(2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol
CAS No.:1235460-11-3
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

Synonyms:(2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

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Chemical Property of (2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

Chemical Property:

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Technology Process of (2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

There total 5 articles about (2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-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:

: 1235459-87-6
(R,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-one

: 1235460-11-3
(2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

: 1235460-12-4
(2R,4R,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

Guidance literature:: With BH₃*DMS; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at 0 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol101103q

Reference yield:

: 2-(pent-2-en-2-yl)-1,3-dithiane

: 1235460-11-3
(2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C

3.1: benzeneseleninic anhydride; methyloxirane / dichloromethane / 16 h / 20 °C / Inert atmosphere

4.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere

4.2: Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; dimethylsulfide borane complex; benzeneseleninic anhydride; methyloxirane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2011.09.069

Reference yield:

: 1235460-05-5
(R,E)-((1-(benzyloxy)-3-(2-(pent-2-en-2-yl)-1,3-dithian-2-yl)propan-2-yl)oxy)(tert-butyl)dimethylsilane

: 1235460-11-3
(2R,4S,E)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)-5-methyloct-5-en-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: benzeneseleninic anhydride; methyloxirane / dichloromethane / 16 h / 20 °C / Inert atmosphere

2.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere

2.2: Inert atmosphere

With dimethylsulfide borane complex; benzeneseleninic anhydride; methyloxirane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tet.2011.09.069