(S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene

Base Information

• Chemical Name: (S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene
• CAS No.: 780782-22-1
• Molecular Formula: C₂₆H₃₅NO₃Si
• Molecular Weight: 437.654
• Mol file: 780782-22-1.mol

Synonyms:(S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene

Chemical Property of (S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene

There total 1 articles about (S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene 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: 99.0%

tert-butylchlorodiphenylsilane (58479-61-1) + tert-butyl (S)-3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate (780782-28-7) → (S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene (780782-22-1)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2004.07.127 DOI:10.1021/jo050519j

Reference yield: 99.0%

(S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene (780782-22-1) → N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In acetone;

DOI:10.1021/jo050519j

Reference yield:

(S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene (780782-22-1) → (3R,4R,5S)-N-tert-butoxycarbonyl-3-(tert-butyldiphenylsilyloxy)-4-hydroxy-5-methylpiperidine (780782-26-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / oxone; aq. Na₂EDTA; CF₃COCH₃ / NaHCO₃ / acetonitrile / 0 °C

2: 71 percent / BF₃*Et₂O; CuCN / diethyl ether / 2 h / -78 °C

With Oxone; 1,1,1-trifluoro-2-propanone; boron trifluoride diethyl etherate; edetate disodium; sodium hydrogencarbonate; In diethyl ether; acetonitrile;

DOI:10.1021/jo050519j

upstream raw materials:

tert-butylchlorodiphenylsilane

tert-butyl (S)-3-hydroxy-3,6-dihydropyridine-1(2H)-carboxylate

Downstream raw materials:

isofagomine

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

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

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

Refernces

• 1、 Ouchi, Hidekazu,Mihara, Yukiko,Watanabe, Hitomi,Takahata, Hiroki. "A short and concise synthesis of isofagomine, homoisofagomine, and 5′-deoxyisofagomine". . p. 7053 - 7056. Retrieved 2007/10/03.