(3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-3-ol

Base Information

Chemical Name:(3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-3-ol
CAS No.:159266-70-3
Molecular Formula:C₃₀H₄₆O₄Si
Molecular Weight:498.778
Hs Code.:

Synonyms:(3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-3-ol

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Chemical Property of (3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-3-ol

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Technology Process of (3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-3-ol

There total 6 articles about (3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-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: 75.0%

: 917-57-7
vinyllithium

: 159266-68-9
(R)-2-((R)-1,2-Bis-benzyloxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-hexanal

: 159266-70-3
(3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-3-ol

Guidance literature:: With copper(l) iodide; tributylphosphine; In diethyl ether; at -78 ℃;
DOI:10.1016/S0040-4039(00)73455-1

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 159266-70-3
(3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to 0 deg C

2: 92 percent / Me₃Al / 0 deg C to room temperature

3: 98 percent / NaH, Bu₄NI / dimethylformamide / 0 deg C to room temperature

4: 93 percent / DIBAL / tetrahydrofuran / 2 h / -78 °C

5: 75 percent / CuI, PBu₃ / diethyl ether / -78 °C

With copper(l) iodide; tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)73455-1

Reference yield:

: (4R,5S)-3-[6-(tert-Butyl-dimethyl-silanyloxy)-hexanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

: 159266-70-3
(3S,4S)-4-((R)-1,2-Bis-benzyloxy-ethyl)-8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to 0 deg C

2: 92 percent / Me₃Al / 0 deg C to room temperature

3: 98 percent / NaH, Bu₄NI / dimethylformamide / 0 deg C to room temperature

4: 93 percent / DIBAL / tetrahydrofuran / 2 h / -78 °C

5: 75 percent / CuI, PBu₃ / diethyl ether / -78 °C

With copper(l) iodide; tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)73455-1