(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester
CAS No.:870651-08-4
Molecular Formula:C₂₀H₃₃NO₄Si
Molecular Weight:379.572
Hs Code.:

Synonyms:(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

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Technology Process of (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

There total 6 articles about (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester 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: 70.0%

: 870651-07-3
3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-piperidine-1-carboxylic acid benzyl ester

: 870651-08-4
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: 3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-piperidine-1-carboxylic acid benzyl ester; With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 3.5h;

With camphor-10-sulfonic acid; In methanol; dichloromethane; at 0 ℃; for 2h; pH=3;
DOI:10.1021/jo051725u

Reference yield:

: 870650-96-7
((1R,2S)-2-Hydroxy-1-hydroxymethyl-hex-5-enyl)-carbamic acid benzyl ester

: 870651-08-4
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 94 percent / 4-(dimethylamino)pyridine; imidazole / CH₂Cl₂ / 40 - 50 °C

2.1: NMO; OsO₄ / acetone; H₂O; toluene / 2 h

2.2: 87 percent / NaIO₄ / CH₂Cl₂ / 1.5 h / 20 °C

3.1: triethylsilane; BF₃*Et₂O / CH₂Cl₂ / 3.5 h / -78 °C

3.2: 70 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 2 h / 0 °C / pH 3

With 1H-imidazole; triethylsilane; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; In dichloromethane; water; acetone; toluene;
DOI:10.1021/jo051725u

Reference yield:

: 870651-04-0
N-benzyloxycarbonyl-(4S)-2,2-dimethyl-4-(1'-oxo-4'-pentenyl)-1,3-oxazolidine

: 870651-08-4
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / CeCl₃*7H₂O; Zn(BH₄)2 / methanol; diethyl ether / 2 h / 0 °C

2.1: 93 percent / Dowex-50W ion-exchange resin / methanol; H₂O / 24 h / 50 °C

3.1: 94 percent / 4-(dimethylamino)pyridine; imidazole / CH₂Cl₂ / 40 - 50 °C

4.1: NMO; OsO₄ / acetone; H₂O; toluene / 2 h

4.2: 87 percent / NaIO₄ / CH₂Cl₂ / 1.5 h / 20 °C

5.1: triethylsilane; BF₃*Et₂O / CH₂Cl₂ / 3.5 h / -78 °C

5.2: 70 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 2 h / 0 °C / pH 3

With 1H-imidazole; triethylsilane; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; zinc(II) tetrahydroborate; Dowex-50W ion-exchange resin; boron trifluoride diethyl etherate; In methanol; diethyl ether; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo051725u