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

Base Information

• Chemical Name: (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine
• CAS No.: 191530-42-4
• Molecular Formula: C₃₇H₄₅N₃O₉
• Molecular Weight: 675.779

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-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: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + (3R,4S,5S,6S)-4-amino-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine (191530-40-2) → (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine (191530-42-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jm960627l

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine (191530-42-4)

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: 91 percent / N,N'-diisopropylethylamine / methanol / 1 h / Ambient temperature

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; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm960627l

Reference yield:

(2S,3R,4S,5R)-2-amino-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-O-isopropylidene-3,4-piperidinediol (176640-82-7) → (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine (191530-42-4)

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: 91 percent / N,N'-diisopropylethylamine / methanol / 1 h / Ambient temperature

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; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/jm960627l

upstream raw materials:

di-tert-butyl dicarbonate

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

benzyl chloroformate

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

Downstream raw materials:

(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-{[(2-methoxyethoxy)methoxy]carbonyl}piperidine

(3R,4S,5S,6S)-6-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-5-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

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