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

Base Information

• Chemical Name: (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-{[(2-methoxyethoxy)methoxy]carbonyl}piperidine
• CAS No.: 191533-49-0
• Molecular Formula: C₂₈H₄₃N₃O₁₁
• Molecular Weight: 597.663
• Mol file: 191533-49-0.mol

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

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

There total 11 articles about (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-{[(2-methoxyethoxy)methoxy]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:

2-Methoxyethoxymethyl chloride (3970-21-6) + (3R,4S,5S,6S)-6-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-5-hydroxy-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (191530-44-6) → (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-{[(2-methoxyethoxy)methoxy]carbonyl}piperidine (191533-49-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1.5h; Yield given;

DOI:10.1021/jm960627l

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3R,4S,5S,6S)-6-[(benzyloxycarbonyl)amino]-1-N-(tert-butoxycarbonyl)-4-[(tert-butoxycarbonyl)amino]-5-hydroxy-3-{[(2-methoxyethoxy)methoxy]carbonyl}piperidine (191533-49-0)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: N,N'-diisopropylethylamine / CH₂Cl₂ / 1.5 h / 0 °C

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

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-{[(2-methoxyethoxy)methoxy]carbonyl}piperidine (191533-49-0)

Guidance literature:

Multi-step reaction with 10 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

10: N,N'-diisopropylethylamine / CH₂Cl₂ / 1.5 h / 0 °C

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:

2-Methoxyethoxymethyl chloride

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

di-tert-butyl dicarbonate

benzyl chloroformate