(3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone

Base Information

Chemical Name:(3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone
CAS No.:140647-94-5
Molecular Formula:C₂₀H₃₈O₅Si
Molecular Weight:386.604
Hs Code.:

Synonyms:(3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone

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Chemical Property of (3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone

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Technology Process of (3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone

There total 5 articles about (3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone 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: 76.0%

: Lithium di(α-ethoxyvinyl)cuprate

: 140647-93-4
(R)-4-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-cyclohex-2-enone

: 140647-94-5
(3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone

Guidance literature:: With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(00)91891-4

Reference yield:

: 16807-60-6
3-methoxycyclohex-2-en-1-one

: 140647-94-5
(3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1: 64 percent / LDA / tetrahydrofuran / -78 °C

2: (i-Pr)2NEt / CH₂Cl₂ / 0 °C

3: 1.) LiAlH₄, 2.) 1 N HCl

4: 76 percent / BF₃*OEt₂ / tetrahydrofuran / -78 °C

With hydrogenchloride; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(00)91891-4

Reference yield:

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 140647-94-5
(3S,4S)-4-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-ethyl]-3-(1-ethoxy-vinyl)-cyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1: 64 percent / LDA / tetrahydrofuran / -78 °C

2: (i-Pr)2NEt / CH₂Cl₂ / 0 °C

3: 1.) LiAlH₄, 2.) 1 N HCl

4: 76 percent / BF₃*OEt₂ / tetrahydrofuran / -78 °C

With hydrogenchloride; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(00)91891-4