(3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide

Base Information

Chemical Name:(3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide
CAS No.:950588-57-5
Molecular Formula:C₂₅H₃₅NO₄Si
Molecular Weight:441.643
Hs Code.:

Synonyms:(3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide

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Chemical Property of (3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide

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Technology Process of (3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide

There total 3 articles about (3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide 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: 97.0%

: 950588-56-4
(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxyhex-4-enoic acid N-methoxy-N-methylamide

: 75-11-6
diiodomethane

: 950588-57-5
(3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide

Guidance literature:: With diethylzinc; In hexane; dichloromethane; at -15 - 20 ℃; for 3h;
DOI:10.1021/ol701564x

Reference yield:

: 950588-55-3
(3R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-1-[(4S)-4-isopropyl-2-thioxothiazolidin-3-yl]hex-4-en-1-one

: 950588-57-5
(3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

2: 97 percent / diethylzinc / CH₂Cl₂; hexane / 3 h / -15 - 20 °C

With 1H-imidazole; diethylzinc; In hexane; dichloromethane; 2: Simmons-Smith cyclopropanation;
DOI:10.1021/ol701564x

Reference yield:

: 131380-48-8
(E)-4-(t-butyldiphenylsilyl)oxy-2-butenal

: 950588-57-5
(3R)-3-{(1R,2R)-2-[(tert-butyldiphenylsilanyloxy)methyl]cyclopropyl}-3-hydroxy-N-methoxy-N-methylpropionamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: titanium tetrachloride; ethyldiisopropylamine / CH₂Cl₂ / 2 h / -78 °C

1.2: 94 percent / CH₂Cl₂ / 6 h / -78 °C

2.1: 71 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

3.1: 97 percent / diethylzinc / CH₂Cl₂; hexane / 3 h / -15 - 20 °C

With 1H-imidazole; diethylzinc; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; 3.1: Simmons-Smith cyclopropanation;
DOI:10.1021/ol701564x