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

Base Information

Chemical Name:2-[(1R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-N,N-dimethyl-acetamide
CAS No.:148933-70-4
Molecular Formula:C₁₇H₃₃NO₃Si
Molecular Weight:327.539
Hs Code.:

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

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

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

There total 7 articles about 2-[(1R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-N,N-dimethyl-acetamide 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: 89.0%

: 18871-66-4
N,N-dimethylacetamide dimethyl acetal

: 168777-83-1
(1S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enol

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

Guidance literature:: In xylene; for 24h; Heating;
DOI:10.1039/c39930000619

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

With 2,6-dimethylpyridine; palladium diacetate; lithium borohydride; chloro-trimethyl-silane; cerium(III) chloride; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; 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

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

Guidance literature:: Multi-step reaction with 6 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

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