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

Base Information

Chemical Name:(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-hydroxymethyl-2-methyl-1-(p-toluenesulfonyl)piperidine
CAS No.:616234-26-5
Molecular Formula:C₃₅H₃₉NO₆S
Molecular Weight:601.764
Hs Code.:

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

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

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

There total 7 articles about (2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-hydroxymethyl-2-methyl-1-(p-toluenesulfonyl)piperidine 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: 98.0%

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

: 616234-26-5
(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-hydroxymethyl-2-methyl-1-(p-toluenesulfonyl)piperidine

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃;
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

: 616234-26-5
(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-hydroxymethyl-2-methyl-1-(p-toluenesulfonyl)piperidine

Guidance literature:: Multi-step reaction with 5 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

5: 98 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

With lithium aluminium tetrahydride; 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

Reference yield:

: C₁₄H₁₉NO₄S^(2-)*H₂Sn⁽²⁺⁾

: 616234-26-5
(2R,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-hydroxymethyl-2-methyl-1-(p-toluenesulfonyl)piperidine

Guidance literature:: Multi-step reaction with 6 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

6: 98 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

With lithium aluminium tetrahydride; 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