(2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde

Base Information

Chemical Name:(2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde
CAS No.:1235543-76-6
Molecular Formula:C₂₃H₃₀O₃Si
Molecular Weight:382.575
Hs Code.:

Synonyms:(2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde

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Chemical Property of (2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde

Chemical Property:

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Technology Process of (2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde

There total 5 articles about (2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde 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:

: 1235543-75-5
((2R,3S)-3-(4-(tert-butyldiphenylsilyloxy)butyl)oxiran-2-yl)methanol

: 1235543-76-6
(2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -80 ℃; Inert atmosphere;

Reference yield:

: 1235543-73-3
tert-butyldiphenyl ((7-((tetrahydro-2H-pyran-2-yl)oxy)hept-5-yn-1-yl)oxy)silane

: 1235543-76-6
(2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / methanol / 20 °C

2.1: sodium tetrahydroborate; hydrogen; nickel(II) acetate tetrahydrate; ethylenediamine / ethanol / 20 °C / 760.05 Torr

3.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 2 h / -20 °C / Molecular sieve; Inert atmosphere

3.2: 48 h / -20 °C / Molecular sieve; Inert atmosphere

4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h / -80 °C / Inert atmosphere

4.2: -80 - 0 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium tetrahydroborate; oxalyl dichloride; diethyl (2S,3S)-tartrate; hydrogen; nickel(II) acetate tetrahydrate; toluene-4-sulfonic acid; ethylenediamine; In methanol; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jm200132q

Reference yield:

: 125010-58-4
(4-bromobutoxy)(tert-butyl)diphenylsilane

: 1235543-76-6
(2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)butyl]oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / -78 - -10 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / methanol / 20 °C

3.1: sodium tetrahydroborate; hydrogen; nickel(II) acetate tetrahydrate; ethylenediamine / ethanol / 20 °C / 760.05 Torr

4.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 2 h / -20 °C / Molecular sieve; Inert atmosphere

4.2: 48 h / -20 °C / Molecular sieve; Inert atmosphere

5.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h / -80 °C / Inert atmosphere

5.2: -80 - 0 °C / Inert atmosphere

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; diethyl (2S,3S)-tartrate; hydrogen; nickel(II) acetate tetrahydrate; toluene-4-sulfonic acid; ethylenediamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jm200132q