(2S)-2-[(2S)-2-amino-2-carboxyethyl]-5-oxooxolane-2-carboxylic acid

Base Information

• Chemical Name: (2S)-2-[(2S)-2-amino-2-carboxyethyl]-5-oxooxolane-2-carboxylic acid
• CAS No.: 69086-72-2
• Molecular Formula: C8H11NO6
• Molecular Weight: 217.17604
• DSSTox Substance ID: DTXSID201173622
• Nikkaji Number: J18.955C
• Mol file: 69086-72-2.mol

Synonyms:69086-72-2;DTXSID201173622;(alphaS,2S)-alpha-Amino-2-carboxytetrahydro-5-oxo-2-furanpropanoic acid;2-Furanpropanoic acid, .alpha.-amino-2-carboxytetrahydro-5-oxo-,[S-(R*,R*)]-

Chemical Property of (2S)-2-[(2S)-2-amino-2-carboxyethyl]-5-oxooxolane-2-carboxylic acid

Chemical Property:

• PSA: 126.92000
• LogP: -0.35090
• XLogP3: -3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 217.05863707
• Heavy Atom Count: 15
• Complexity: 314

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1=O)(CC(C(=O)O)N)C(=O)O
• Isomeric SMILES: C1C[C@](OC1=O)(C[C@@H](C(=O)O)N)C(=O)O
• General Description: (+)-Lycoperdic acid is an unusual mushroom-derived amino acid, specifically a 4-hydroxyglutamic acid derivative, isolated from the edible mushroom *Lycoperdon perlatum*. It features a tetrahydrofuran ring with a 2-amino-2-carboxyethyl substituent and a carboxylic acid group at the 2-position. (+)-Lycoperdic acid has been synthesized stereoselectively, with key steps involving asymmetric hydrogenation and oxidative cleavage strategies, confirming its structural and stereochemical properties.

Technology Process of (2S)-2-[(2S)-2-amino-2-carboxyethyl]-5-oxooxolane-2-carboxylic acid

There total 46 articles about (2S)-2-[(2S)-2-amino-2-carboxyethyl]-5-oxooxolane-2-carboxylic 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: 77.0%

methyl (5S,8S)-7-tert-butoxycarbonyl-2,6-dioxo-1-oxa-7-azaspiro<4.4>nonane-8-carboxylate (146554-64-5) → (+)-lycoperdic acid (69086-72-2)

Guidance literature:

With hydrogenchloride; for 12h; Heating;

DOI:10.1016/S0040-4039(00)74730-7

Reference yield: 64.0%

benzoic (5S,8S)-2,6-dioxo-1-oxa-7-aza-spiro[4.4]nonane-8-carboxylic anhydride (502698-24-0) → (+)-lycoperdic acid (69086-72-2)

Guidance literature:

With hydrogenchloride; for 24h; Heating;

DOI:10.1016/S0040-4020(02)01254-1

Reference yield:

C17H29NO9 → (+)-lycoperdic acid (69086-72-2) + (2S,5'R)-2-amino-3-(5'-carboxy-2'-oxo-5'-tetrahydrofuranyl)propanoic acid

Guidance literature:

C₁₇H₂₉NO₉; With hydrogenchloride; water; In dichloromethane; for 8h; Molecular sieve;

In water; acetic acid; Overall yield = 66 %; Overall yield = 87 mg;

DOI:10.1016/j.tet.2015.10.014

upstream raw materials:

methyl (5S,8S)-7-tert-butoxycarbonyl-2,6-dioxo-1-oxa-7-azaspiro<4.4>nonane-8-carboxylate

benzoic (5S,8S)-2,6-dioxo-1-oxa-7-aza-spiro[4.4]nonane-8-carboxylic anhydride

4-(hydroxymethyl)pent-4-enoic acid ethyl ester

(2S,4S)-4-(tert-butoxycarbonyl)amino-2-[2-(ethoxycarbonyl)ethyl]-2-(hydroxymethyl)oxolan-5-one