(S)-2-(BENZYLOXYCARBONYLAMINO)-5-(1,3-DIOXOLAN-2-YL)PENTANOIC ACID

Base Information

• Chemical Name: (S)-2-(BENZYLOXYCARBONYLAMINO)-5-(1,3-DIOXOLAN-2-YL)PENTANOIC ACID
• CAS No.: 852822-01-6
• Molecular Formula: C16H21NO6
• Molecular Weight: 323.346
• Mol file: 852822-01-6.mol

Synonyms:(S)-2-(BENZYLOXYCARBONYLAMINO)-5-(1,3-DIOXOLAN-2-YL)PENTANOIC ACID;CBZ-L-ALLYSINE ETHYLENE ACETAL;Z-AEA-OH

Chemical Property of (S)-2-(BENZYLOXYCARBONYLAMINO)-5-(1,3-DIOXOLAN-2-YL)PENTANOIC ACID

Chemical Property:

• PSA: 94.09000
• LogP: 2.30010

Purity/Quality:

Cbz-L-allysine ethylene acetal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-(BENZYLOXYCARBONYLAMINO)-5-(1,3-DIOXOLAN-2-YL)PENTANOIC ACID

There total 1 articles about (S)-2-(BENZYLOXYCARBONYLAMINO)-5-(1,3-DIOXOLAN-2-YL)PENTANOIC ACID 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%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (S)-2-amino-5-(1,3-dioxolane-2-yl)-pentanoic acid (215054-80-1,170242-34-9) → (S)-2-Benzyloxycarbonylamino-5-[1,3]dioxolan-2-yl-pentanoic acid (852822-01-6)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; In 1,4-dioxane;

DOI:10.1021/ol047774v

Reference yield: 97.0%

(S)-2-Benzyloxycarbonylamino-5-[1,3]dioxolan-2-yl-pentanoic acid (852822-01-6) + methyl iodide (74-88-4) → (S)-2-benzyloxycarbonylamino-5-(2-[1,3]dioxolanyl)-pentanoic acid methyl ester (824943-43-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/ol047774v

Reference yield:

(S)-2-Benzyloxycarbonylamino-5-[1,3]dioxolan-2-yl-pentanoic acid (852822-01-6) → (2S,5R)-5-hydroxy-piperidine-2-carboxylic acid hydrochloride (824943-40-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / K₂CO₃ / dimethylformamide / 2 h / 20 °C

2: 98 percent / TsOH*H₂ODMF / toluene / 2 h / 115 °C

3: 90 percent / Oxone(R); NaHCO₃ / 20 °C

4: H₂ / Pd/C / methanol / 1.5 h

5: 57 mg / aq. HCl / 2.5 h / Heating

With hydrogenchloride; oxone; hydrogen; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol047774v

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

(S)-2-amino-5-(1,3-dioxolane-2-yl)-pentanoic acid

Downstream raw materials:

(S)-2-benzyloxycarbonylamino-5-(2-[1,3]dioxolanyl)-pentanoic acid methyl ester

(2S)-3,4-dihydro-2H-pyridine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2S,5R)-5-hydroxy-6-methoxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

(2S,5R)-5-acetoxy-6-methoxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester