2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide

Base Information

Chemical Name:2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide
CAS No.:1268868-58-1
Molecular Formula:C₃₁H₄₅NO₅Si
Molecular Weight:539.788
Hs Code.:

Synonyms:2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide

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Chemical Property of 2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide

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Technology Process of 2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide

There total 3 articles about 2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide 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%

: 951396-65-9
(1R,4S,6R)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

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

: 1268868-58-1
2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide

Guidance literature:: In o-xylene; at 150 ℃; for 23h; stereoselective reaction; Sealed tube; Inert atmosphere;
DOI:10.3987/COM-10-S(E)27

Reference yield:

: 951396-66-0
C₂₇H₃₈O₅Si

: 1268868-58-1
2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridinium chlorochromate / dichloromethane / 1 h / 60 °C / Molecular sieve

1.2: Silica gel / 0.08 h / 25 °C

2.1: cerium(III) chloride heptahydrate / dichloromethane; methanol / 1 h / 20 °C

2.2: 0.5 h / -78 °C

3.1: o-xylene / 23 h / 150 °C / Sealed tube; Inert atmosphere

With cerium(III) chloride heptahydrate; pyridinium chlorochromate; In methanol; dichloromethane; o-xylene; 2.1: |Claisen Rearrangement / 2.2: |Claisen Rearrangement / 3.1: |Eschenmoser-Claisen Rearrangement;
DOI:10.3987/COM-10-S(E)27

Reference yield:

: 951396-67-1
(4S,6R)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-one

: 1268868-58-1
2-[(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-yl]-N,N-dimethylacetamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: cerium(III) chloride heptahydrate / dichloromethane; methanol / 1 h / 20 °C

1.2: 0.5 h / -78 °C

2.1: o-xylene / 23 h / 150 °C / Sealed tube; Inert atmosphere

With cerium(III) chloride heptahydrate; In methanol; dichloromethane; o-xylene; 1.1: |Claisen Rearrangement / 1.2: |Claisen Rearrangement / 2.1: |Eschenmoser-Claisen Rearrangement;
DOI:10.3987/COM-10-S(E)27