tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

Base Information

Chemical Name:tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate
CAS No.:616234-25-4
Molecular Formula:C₃₉H₄₅NO₇S
Molecular Weight:671.855
Hs Code.:

Synonyms:tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

Suppliers and Price of tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

There total 5 articles about tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate 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%

: 100-39-0
benzyl bromide

: 616234-24-3
tert-butyl (2S,3R,4S,5R)-3,4,5-trihydroxy-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

: 616234-25-4
tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1002/ejoc.200300079

Reference yield:

: C₁₄H₁₉NO₄S^(2-)*H₂Sn⁽²⁺⁾

: 616234-25-4
tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / tetrahydrofuran / -78 °C

2: 100 percent / hydrogen / Pd/C / methanol / 20 °C / 2250.18 Torr

3: 72 percent / DEAD; PPh₃ / tetrahydrofuran / 20 °C

4: 100 percent / Dowex 50WX₈ / methanol; H₂O / 10 h / 20 °C

5: 99 percent / tetra-n-butylammonium iodide; NaH / dimethylformamide / 0 - 20 °C

With dowex 50Wx₈; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1: aldol reaction / 3: Mitsunobu cyclization;
DOI:10.1002/ejoc.200300079

Reference yield:

: (2S,3R)-3-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-2-(toluene-4-sulfonylamino)-propionic acid tert-butyl ester

: 616234-25-4
tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / hydrogen / Pd/C / methanol / 20 °C / 2250.18 Torr

2: 72 percent / DEAD; PPh₃ / tetrahydrofuran / 20 °C

3: 100 percent / Dowex 50WX₈ / methanol; H₂O / 10 h / 20 °C

4: 99 percent / tetra-n-butylammonium iodide; NaH / dimethylformamide / 0 - 20 °C

With dowex 50Wx₈; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 2: Mitsunobu cyclization;
DOI:10.1002/ejoc.200300079