(2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine

Base Information

Chemical Name:(2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine
CAS No.:350246-31-0
Molecular Formula:C₃₀H₄₅NO₇SSi
Molecular Weight:591.841
Hs Code.:

Synonyms:(2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine

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Chemical Property of (2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine

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Technology Process of (2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine

There total 16 articles about (2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine 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%

: 98-59-9
p-toluenesulfonyl chloride

: 350246-30-9
(2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-hydroxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine

: 350246-31-0
(2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 3h;
DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2

Reference yield:

: 220861-39-2
(R)-3-((tert-butyldimethylsilyl)oxy)pent-4-enal

: 350246-31-0
(2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / H₂NOH*HCl / aq. ethanol / 14 h / 20 °C

2.1: sodium cyanoborohydride; HCl / methanol / 0.5 h / -10 °C

3.1: MgSO₄ / CH₂Cl₂ / 1 h / 0 °C

4.1: 2.25 g / toluene / 24 h / 70 °C

5.1: H₂ / 20percent Pd/C / methanol / 48 h

6.1: 2.88 g / NaHCO₃ / diethyl ether / 20 h / 0 °C

7.1: 72 percent / nBu₃P / tetrahydrofuran / 2 h

8.1: 85 percent / mCPBA / CH₂Cl₂ / 0.08 h

9.1: O₃ / CH₂Cl₂

9.2: 88 percent / PPh₃ / CH₂Cl₂ / 2 h / 20 °C

10.1: 90 percent / diethyl ether; tetrahydrofuran / 2 h / 0 °C

11.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h

With hydrogenchloride; dmap; tributylphosphine; hydroxylamine hydrochloride; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; magnesium sulfate; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; 20percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2

Reference yield:

: C₂₂H₃₅NO₄Si

: 350246-31-0
(2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-tosyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2.25 g / toluene / 24 h / 70 °C

2.1: H₂ / 20percent Pd/C / methanol / 48 h

3.1: 2.88 g / NaHCO₃ / diethyl ether / 20 h / 0 °C

4.1: 72 percent / nBu₃P / tetrahydrofuran / 2 h

5.1: 85 percent / mCPBA / CH₂Cl₂ / 0.08 h

6.1: O₃ / CH₂Cl₂

6.2: 88 percent / PPh₃ / CH₂Cl₂ / 2 h / 20 °C

7.1: 90 percent / diethyl ether; tetrahydrofuran / 2 h / 0 °C

8.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h

With dmap; tributylphosphine; hydrogen; sodium hydrogencarbonate; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; 20percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2