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

Base Information

• Chemical Name: (3R,4S,5S,6S)-6-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-5-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester
• CAS No.: 191530-44-6
• Molecular Formula: C₂₄H₃₅N₃O₉
• Molecular Weight: 509.557
• Mol file: 191530-44-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (3R,4S,5S,6S)-6-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-5-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 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:

(3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-[(diphenylmethoxy)carbonyl]piperidine (191530-42-4) → (3R,4S,5S,6S)-6-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-5-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (191530-44-6)

Guidance literature:

With sodium hydroxide; In methanol; for 1.5h; Ambient temperature;

DOI:10.1021/jm960627l

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3R,4S,5S,6S)-6-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-5-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (191530-44-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: aq. NaOH / methanol / 1.5 h / Ambient temperature

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; In methanol;

DOI:10.1021/jm960627l

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3R,4S,5S,6S)-6-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-5-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (191530-44-6)

Guidance literature:

Multi-step reaction with 9 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

9: aq. NaOH / methanol / 1.5 h / Ambient temperature

With pyridine; ruthenium(IV) oxide; sodium hydroxide; 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:

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

di-tert-butyl dicarbonate

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