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

Base Information

Chemical Name:(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(N,N'-bis(tert-butoxycarbonyl)guanidino)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine
CAS No.:191530-53-7
Molecular Formula:C₄₃H₅₅N₅O₁₁
Molecular Weight:817.937
Hs Code.:

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

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

There total 8 articles about (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(N,N'-bis(tert-butoxycarbonyl)guanidino)-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: 98.0%

: 145013-05-4
tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate

: 191530-40-2
(3R,4S,5S,6S)-4-amino-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

: 191530-53-7
(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(N,N'-bis(tert-butoxycarbonyl)guanidino)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

Guidance literature:: With triethylamine; mercury dichloride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1021/jm960627l

Reference yield:

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

: 191530-53-7
(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(N,N'-bis(tert-butoxycarbonyl)guanidino)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

Guidance literature:: Multi-step reaction with 8 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

7: 68 percent / NaBH₄ / ethanol / 0.83 h / Ambient temperature

8: 98 percent / HgCl₂, Et₃N / dimethylformamide / 1 h / 0 °C

With pyridine; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; potassium tert-butylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; 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

: 191530-53-7
(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-(N,N'-bis(tert-butoxycarbonyl)guanidino)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine

Guidance literature:: Multi-step reaction with 8 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

7: 68 percent / NaBH₄ / ethanol / 0.83 h / Ambient temperature

8: 98 percent / HgCl₂, Et₃N / dimethylformamide / 1 h / 0 °C

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