(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

Base Information

Chemical Name:(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine
CAS No.:191530-38-8
Molecular Formula:C₃₄H₃₆Cl₃N₃O₈
Molecular Weight:721.034
Hs Code.:

Synonyms:(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

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Chemical Property of (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

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Technology Process of (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

There total 6 articles about (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]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: 95.0%

: 192211-49-7
(3aS,4R,7S,7aS)-7-[(benzyloxycarbonyl)amino]-6-N-(tert-butoxycarbonyl)-2-(trichloromethyl)-4-[(diphenylmethoxy)carbonyl]-3a,7a-dihydrooxazolo[5,4-c]piperidine

: 191530-38-8
(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

Guidance literature:: With pyridine; toluene-4-sulfonic acid; at 80 ℃; for 2h;
DOI:10.1021/jm960627l

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 191530-38-8
(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / N,N-diisopropylethylamine / methanol / 1.5 h / 0 °C

2: 80 percent / aq. NaIO₄, RuO₂ / CCl₄; acetonitrile / 0.67 h / Ambient temperature

3: 94 percent / CH₂Cl₂; methanol / Ambient temperature

4: 70 percent / t-BuOK / tetrahydrofuran / 2 h / 0 °C

5: 70 percent / DBU / CH₂Cl₂ / 0.08 h / Ambient temperature

6: 95 percent / aq. p-toluenesulfonic acid, pyridine / 2 h / 80 °C

With pyridine; ruthenium(IV) oxide; sodium periodate; potassium tert-butylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; acetonitrile;
DOI:10.1021/jm960627l

Reference yield:

: 176640-82-7
(2S,3R,4S,5R)-2-amino-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-O-isopropylidene-3,4-piperidinediol

: 191530-38-8
(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(trichloroacetamido)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / N,N-diisopropylethylamine / methanol / 1.5 h / 0 °C

2: 80 percent / aq. NaIO₄, RuO₂ / CCl₄; acetonitrile / 0.67 h / Ambient temperature

3: 94 percent / CH₂Cl₂; methanol / Ambient temperature

4: 70 percent / t-BuOK / tetrahydrofuran / 2 h / 0 °C

5: 70 percent / DBU / CH₂Cl₂ / 0.08 h / Ambient temperature

6: 95 percent / aq. p-toluenesulfonic acid, pyridine / 2 h / 80 °C

With pyridine; ruthenium(IV) oxide; sodium periodate; potassium tert-butylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; acetonitrile;
DOI:10.1021/jm960627l