L-Allysine ethylene acetal

Base Information

• Chemical Name: L-Allysine ethylene acetal
• CAS No.: 215054-80-1
• Molecular Formula: C8H15NO4
• Molecular Weight: 189.211
• Hs Code.: 2932999099
• European Community (EC) Number: 606-785-1
• DSSTox Substance ID: DTXSID801262449
• Nikkaji Number: J1.255.141J
• Mol file: 215054-80-1.mol

Synonyms:allysine ethylene acetal

Chemical Property of L-Allysine ethylene acetal

Chemical Property:

• Melting Point: >200 °C (decomp)
• Boiling Point: 338.72 °C at 760 mmHg
• PKA: 2.53±0.24(Predicted)
• Flash Point: 158.653 °C
• PSA: 81.78000
• Density: 1.208 g/cm³
• LogP: 0.64180
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 189.10010796
• Heavy Atom Count: 13
• Complexity: 168

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-Allysine ethylene acetal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1COC(O1)CCCC(C(=O)O)N
• Isomeric SMILES: C1COC(O1)CCC[C@@H](C(=O)O)N

Technology Process of L-Allysine ethylene acetal

There total 2 articles about L-Allysine ethylene acetal 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: 30.0%

N-benzoyl allysine ethylene acetal (226725-71-9) → (R)-N-benzoyl allysine ethylene acetal (1258790-30-5) + (S)-2-amino-5-(1,3-dioxolane-2-yl)-pentanoic acid (215054-80-1,170242-34-9)

Guidance literature:

With sodium hydroxide; In water; at 65 ℃; for 5h; pH=7.5; Large scale reaction; Enzymatic reaction;

DOI:10.1021/op100258j

Reference yield:

2-amino-5-(1,3-dioxolane-2-yl)-pentanoic acid amide → L-allysine acetal + (S)-2-amino-5-(1,3-dioxolane-2-yl)-pentanoic acid (215054-80-1,170242-34-9)

Guidance literature:

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

upstream raw materials:

N-benzoyl allysine ethylene acetal

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-5-[1,3]dioxolan-2-yl-pentanoic acid

(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

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

Refernces

Diastereoselective synthesis of (2Ss,5R)-5-hydroxypipecolic acid and 6-substituted derivatives

10.1021/ol047774v

The study presents a diastereoselective synthesis method for the natural product (2S,5R)-5-hydroxypipecolic acid and its 6-substituted derivatives. The key step involves a highly diastereoselective epoxidation reaction of an enantiomerically pure cyclic enamide intermediate. Chemicals used include L-allysine ethylene acetal 4, Cbz-OSu for N-carbonylation, MeI for methylation, ptoluenesulfonic acid for cyclization-elimination, and oxone for epoxidation. The synthesis also involves N-acyliminium ion chemistry for the introduction of substituents at the 6-position. These chemicals serve to protect the amino acid, facilitate cyclization, and achieve the desired diastereoselectivity in the formation of the target compounds, which are important due to their presence in various plants, microorganisms, and as the core structure of numerous naturally occurring alkaloids.

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