(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine

Base Information

Chemical Name:(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine
CAS No.:866923-70-8
Molecular Formula:C₂₇H₃₉NO₅Si
Molecular Weight:485.696
Hs Code.:

Synonyms:(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine

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Chemical Property of (3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine

Chemical Property:

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Technology Process of (3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine

There total 12 articles about (3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)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:

: 3-(tert-butyl-diphenyl-silanyloxy)-5-formyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

: 866923-70-8
(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine

Guidance literature:: With sodium tetrahydroborate; In ethanol; water; at 20 ℃; for 1h;
DOI:10.1021/jo050519j

Reference yield:

: 224779-27-5
tert-butyl 3-hydroxy-1,2,3,6-tetrahydropyridine-N-carboxylate

: 866923-70-8
(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine

Guidance literature:: Multi-step reaction with 7 steps

1: 49 percent / Pseudomonas cepacia lipase/ceramics / various solvent(s) / 18 h / 40 °C

2: 98 percent / Pseudomonas cepacia lipase/ceramics; aq. phosphate buffer / acetone / 18 h / 40 °C / pH 7.0

3: 99 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

4: 72 percent / oxone; aq. Na₂EDTA; CF₃COCH₃ / NaHCO₃ / acetonitrile / 0 °C

5: 80 percent / n-BuLi; CuCN; BF₃*Et₂O / diethyl ether; hexane / 2 h / -78 °C

6: OsO₄; NaIO₄ / ethanol; H₂O / 24 h / 20 °C

7: 216 mg / NaBH₄ / ethanol; H₂O / 1 h / 20 °C

With 1H-imidazole; dmap; Oxone; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; phosphate buffer; Pseudomonas cepacia lipase; 1,1,1-trifluoro-2-propanone; ceramics; boron trifluoride diethyl etherate; edetate disodium; sodium hydrogencarbonate; In diethyl ether; ethanol; hexane; dichloromethane; water; acetone; acetonitrile;
DOI:10.1021/jo050519j

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 866923-70-8
(3S,4S,5R)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-(hydroxymethyl)piperidine

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 72 percent / oxone; aq. Na₂EDTA; CF₃COCH₃ / NaHCO₃ / acetonitrile / 0 °C

3: 80 percent / n-BuLi; CuCN; BF₃*Et₂O / diethyl ether; hexane / 2 h / -78 °C

4: OsO₄; NaIO₄ / ethanol; H₂O / 24 h / 20 °C

5: 216 mg / NaBH₄ / ethanol; H₂O / 1 h / 20 °C

With 1H-imidazole; dmap; Oxone; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; 1,1,1-trifluoro-2-propanone; boron trifluoride diethyl etherate; edetate disodium; sodium hydrogencarbonate; In diethyl ether; ethanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo050519j