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

Base Information

• Chemical Name: tert-butyl (2S,3R,4S,5R)-3,4,5-trihydroxy-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate
• CAS No.: 616234-24-3
• Molecular Formula: C₁₈H₂₇NO₇S
• Molecular Weight: 401.481
• Mol file: 616234-24-3.mol

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

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

There total 4 articles about tert-butyl (2S,3R,4S,5R)-3,4,5-trihydroxy-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: 100.0%

(3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester (616234-23-2) → tert-butyl (2S,3R,4S,5R)-3,4,5-trihydroxy-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate (616234-24-3)

Guidance literature:

With dowex 50Wx₈; In methanol; water; at 20 ℃; for 10h;

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

Guidance literature:

Multi-step reaction with 3 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

With dowex 50Wx₈; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; 2: Mitsunobu cyclization;

DOI:10.1002/ejoc.200300079

Reference yield:

C14H19NO4S(2-)*H2Sn(2+) → tert-butyl (2S,3R,4S,5R)-3,4,5-trihydroxy-2-methyl-1-(p-toluenesulfonyl)piperidine-2-carboxylate (616234-24-3)

Guidance literature:

Multi-step reaction with 4 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

With dowex 50Wx₈; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; 1: aldol reaction / 3: Mitsunobu cyclization;

DOI:10.1002/ejoc.200300079

upstream raw materials:

(3aR,6S,7R,7aR)-7-Hydroxy-2,2,6-trimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine-6-carboxylic acid tert-butyl ester

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

Downstream raw materials:

(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-1-[2'-(diethoxyphosphoryl)acetyl]-2-hydroxymethyl-2-methylpiperidine

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

tert-butyl (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methylpiperidine-2-carboxylate

(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-hydroxymethyl-2-methylpiperidine