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

Base Information

• Chemical Name: (2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-hydroxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine
• CAS No.: 350246-30-9
• Molecular Formula: C₂₃H₃₉NO₅Si
• Molecular Weight: 437.652

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-hydroxypropyl)-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: 90.0%

methylmagnesium bromide (75-16-1) + (2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one (350246-29-6) → (2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-hydroxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine (350246-30-9)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 0 ℃; for 2h;

DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2

Reference yield:

(R)-3-((tert-butyldimethylsilyl)oxy)pent-4-enal (220861-39-2) → (2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-hydroxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine (350246-30-9)

Guidance literature:

Multi-step reaction with 10 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

With hydrogenchloride; tributylphosphine; hydroxylamine hydrochloride; hydrogen; sodium cyanoborohydride; sodium hydrogencarbonate; magnesium sulfate; ozone; 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:

N-[3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-hydroxylamine → (2S,3R,4R)-N-Benzyloxycarbonyl-2-(3-hydroxypropyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-3-methylpiperidine (350246-30-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: MgSO₄ / CH₂Cl₂ / 1 h / 0 °C

2.1: 2.25 g / toluene / 24 h / 70 °C

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

4.1: 2.88 g / NaHCO₃ / diethyl ether / 20 h / 0 °C

5.1: 72 percent / nBu₃P / tetrahydrofuran / 2 h

6.1: 85 percent / mCPBA / CH₂Cl₂ / 0.08 h

7.1: O₃ / CH₂Cl₂

7.2: 88 percent / PPh₃ / CH₂Cl₂ / 2 h / 20 °C

8.1: 90 percent / diethyl ether; tetrahydrofuran / 2 h / 0 °C

With tributylphosphine; hydrogen; sodium hydrogencarbonate; magnesium sulfate; ozone; 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

upstream raw materials:

methylmagnesium bromide

(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one

tert-butyldimethylsilyl chloride

benzyl chloroformate

Downstream raw materials:

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

(8R,8aS)-6-((E)-(2R,6S)-6-Benzyloxymethoxy-1-hydroxy-2,5-dimethyl-oct-4-enyl)-8-hydroxy-8-methyl-hexahydro-indolizin-7-one

(8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done

(7S,8R,8aS,6E)-7,8-Dihydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizidine

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