(3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde

Base Information

Chemical Name:(3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde
CAS No.:1449674-39-8
Molecular Formula:C₁₆H₃₀O₃Si
Molecular Weight:298.498
Hs Code.:

Synonyms:(3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde

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Chemical Property of (3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde

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Technology Process of (3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde

There total 11 articles about (3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde 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: 90.0%

: (1S,2S,4S,6R)-4-((tert-butyldimethylsilyl)oxy)-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptane-2-carbaldehyde

: 1449674-39-8
(3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde

Guidance literature:: With pyrrolidine; In diethyl ether; at 20 ℃;
DOI:10.1039/c3ob41226a

Reference yield:

: 1449674-47-8
C₁₇H₂₈O₄

: 1449674-39-8
(3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C / Inert atmosphere

2: bis(cyclopentadienyl)titanium dichloride; manganese / tetrahydrofuran / 6 h / 40 °C / Inert atmosphere

3: sodium hydroxide / water; methanol / 20 °C

4: triethylamine / dichloromethane / -40 °C

5: 2,6-dimethylpyridine / dichloromethane / 20 °C

6: sodium hydroxide / water; methanol / 20 °C

7: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

8: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

9: pyrrolidine / diethyl ether / 20 °C

With pyrrolidine; 2,6-dimethylpyridine; bis(cyclopentadienyl)titanium dichloride; manganese; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1039/c3ob41226a

Reference yield:

: 86561-83-3
(S,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol

: 1449674-39-8
(3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: zirconium(IV) chloride / dichloromethane / 0.17 h / 20 °C

2: triethylamine / dichloromethane / -40 °C

3: 2,6-dimethylpyridine / dichloromethane / 20 °C

4: sodium hydroxide / water; methanol / 20 °C

5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

6: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

7: pyrrolidine / diethyl ether / 20 °C

With pyrrolidine; 2,6-dimethylpyridine; zirconium(IV) chloride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1039/c3ob41226a