2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol

Base Information

Chemical Name:2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol
CAS No.:148933-84-0
Molecular Formula:C₁₅H₃₀O₃Si
Molecular Weight:286.487
Hs Code.:

Synonyms:2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol

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Chemical Property of 2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol

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Technology Process of 2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol

There total 8 articles about 2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol 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: 92.0%

: 148933-70-4
2-[(1R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-N,N-dimethyl-acetamide

: 148933-84-0
2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at 0 - 25 ℃; for 2h;
DOI:10.1039/c39930000619

Reference yield:

: (1S,2R,6S)-2-(benzyloxy)-7-oxabicyclo[4.1.0]heptane

: 148933-84-0
2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / camphorsulfonic acid (CSA) / 2 h / 25 °C

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

3: 95 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 2 h / 25 °C

4: 92 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 - -10 °C

5: 1.) lithium diisopropylamide (LDA), TMSCl, 2.) Pd(OAc)2 / 1.) THF, -78 deg C, 0.5 h, 2.) MeCN, 50 deg C, 18 h

6: 95 percent / LiBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.5 h / -78 °C

7: 89 percent / xylene / 24 h / Heating

8: 92 percent / LiEt₃BH / tetrahydrofuran / 2 h / 0 - 25 °C

With 2,6-dimethylpyridine; palladium diacetate; lithium borohydride; chloro-trimethyl-silane; cerium(III) chloride; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; xylene;
DOI:10.1039/c39930000619

Reference yield:

: (1S,2R,6R)-2-Benzyloxy-6-methoxy-cyclohexanol

: 148933-84-0
2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

2: 95 percent / H₂ / 20percent Pd(OH)2/C / ethanol / 2 h / 25 °C

3: 92 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 - -10 °C

4: 1.) lithium diisopropylamide (LDA), TMSCl, 2.) Pd(OAc)2 / 1.) THF, -78 deg C, 0.5 h, 2.) MeCN, 50 deg C, 18 h

5: 95 percent / LiBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.5 h / -78 °C

6: 89 percent / xylene / 24 h / Heating

7: 92 percent / LiEt₃BH / tetrahydrofuran / 2 h / 0 - 25 °C

With 2,6-dimethylpyridine; palladium diacetate; lithium borohydride; chloro-trimethyl-silane; cerium(III) chloride; oxalyl dichloride; hydrogen; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; xylene;
DOI:10.1039/c39930000619