(1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol

Base Information

Chemical Name:(1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol
CAS No.:1266251-33-5
Molecular Formula:C₂₀H₃₆O₄Si
Molecular Weight:368.589
Hs Code.:

Synonyms:(1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol

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Chemical Property of (1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol

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Technology Process of (1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol

There total 8 articles about (1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol 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: 85.0%

: 1266251-32-4
(4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enone

: 1266251-33-5
(1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol

Guidance literature:: With sodium tetrahydroborate; CeCl₃H₂O; In methanol; at -78 ℃; for 0.5h; Inert atmosphere;
DOI:10.1007/s12039-010-0066-z

Reference yield:

: 921770-78-7
(6S)-6-[(2S)-1,4-dioxa-spiro[4.5]dec-2-yl]octa-1,7-dien-4-ol

: 1266251-33-5
(1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol

Guidance literature:: Multi-step reaction with 7 steps

1: Grubbs catalyst first generation / dichloromethane / 6 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: lithium hydrochloride monohydrate / methanol / 3 h / -5 °C / Inert atmosphere

5: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

6: triethylamine / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

7: sodium tetrahydroborate; CeCl₃H₂O / methanol / 0.5 h / -78 °C / Inert atmosphere

With Grubbs catalyst first generation; dmap; sodium tetrahydroborate; CeCl₃H₂O; lithium hydrochloride monohydrate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1007/s12039-010-0066-z

Reference yield:

: 1266251-28-8
(S)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-3-enyl acetate

: 1266251-33-5
(1R,4S,5R)-4-(tert-butyldimethylsilyloxy)-5-((S)-1,4-dioxaspiro[4.5]decan-2-yl)cyclohex-2-enol

Guidance literature:: Multi-step reaction with 5 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: lithium hydrochloride monohydrate / methanol / 3 h / -5 °C / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: triethylamine / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

5: sodium tetrahydroborate; CeCl₃H₂O / methanol / 0.5 h / -78 °C / Inert atmosphere

With sodium tetrahydroborate; CeCl₃H₂O; lithium hydrochloride monohydrate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1007/s12039-010-0066-z