(2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine

Base Information

Chemical Name:(2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine
CAS No.:317809-52-2
Molecular Formula:C₂₃H₃₉NO₇Si
Molecular Weight:469.651
Hs Code.:

Synonyms:(2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine

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Chemical Property of (2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine

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Technology Process of (2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine

There total 6 articles about (2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine 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:

: 317809-51-1
(R)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-1-(benzyloxycarbonyl)-1,2,3,6-tetrahydro-pyridine

: 317809-52-2
(2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; at 0 - 20 ℃;
DOI:10.1021/ol000188r

Reference yield:

: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

: 317809-52-2
(2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide; various solvent(s) / 0.5 h / 0 - 20 °C

1.2: 83 percent / PPh₃ / Pd(OAc)2 / dimethylformamide; various solvent(s) / 15 h

2.1: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

3.1: 95 percent / CH₂=CH₂ / PhCH=RuCl₂(PCy₃)2 / CH₂Cl₂ / 24 h / 20 °C

4.1: K₂CO₃; PhSH / dimethylformamide / 7 h / 20 - 45 °C

5.1: 642 mg / dimethylformamide / 20 °C

6.1: OsO₄; NMO / acetone; H₂O / 0 - 20 °C

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; ethene; sodium hydride; potassium carbonate; thiophenol; Grubbs catalyst first generation; In dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: deprotonation / 1.2: Alkylation / 2.1: silylation / 3.1: Rearrangement / 4.1: Hydrolysis / 5.1: Acylation / 6.1: hydroxylation;
DOI:10.1021/ol000188r

Reference yield:

: 317809-48-6
N-but-3-enyl-N-((1R,4S)-4-hydroxy-cyclopent-2-enyl)-2-nitro-benzenesulfonamide

: 317809-52-2
(2R,3R,4S)-2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-1-(benzyloxycarbonyl)-3,4-dihydroxy-piperidine

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

2: 95 percent / CH₂=CH₂ / PhCH=RuCl₂(PCy₃)2 / CH₂Cl₂ / 24 h / 20 °C

3: K₂CO₃; PhSH / dimethylformamide / 7 h / 20 - 45 °C

4: 642 mg / dimethylformamide / 20 °C

5: OsO₄; NMO / acetone; H₂O / 0 - 20 °C

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; ethene; potassium carbonate; thiophenol; Grubbs catalyst first generation; In dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: silylation / 2: Rearrangement / 3: Hydrolysis / 4: Acylation / 5: hydroxylation;
DOI:10.1021/ol000188r