Acromelic acid B

Base Information

• Chemical Name: Acromelic acid B
• CAS No.: 86630-10-6
• Molecular Formula: C₁₃H₁₄N₂O₇
• Molecular Weight: 310.263
• UNII: V0973I7148
• DSSTox Substance ID: DTXSID40235733
• Nikkaji Number: J413.584I
• Wikidata: Q27291372
• Metabolomics Workbench ID: 102151
• ChEMBL ID: CHEMBL4776799
• Mol file: 86630-10-6.mol

Synonyms:acromelic acid B

Chemical Property of Acromelic acid B

Chemical Property:

• Vapor Pressure: 8.75E-24mmHg at 25°C
• Boiling Point: 737.3°Cat760mmHg
• Flash Point: 399.7°C
• PSA: 157.05000
• Density: 1.577g/cm³
• LogP: 0.04510
• XLogP3: -4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 310.08010079
• Heavy Atom Count: 22
• Complexity: 608

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(N1)C(=O)O)CC(=O)O)C2=C(NC(=O)C=C2)C(=O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H](N1)C(=O)O)CC(=O)O)C2=C(NC(=O)C=C2)C(=O)O

Technology Process of Acromelic acid B

There total 46 articles about Acromelic acid B 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: 99.0%

2-((2R,3S,4S)-1-((benzyloxy)carbonyl)-2-(tert-butoxycarbonyl)-4-(2-(tert-butoxycarbonyl)-6-methoxypyridin-3-yl)-pyrrolidin-3-yl)acetic acid (1585241-77-5) → acromelic acid B (86630-10-6)

Guidance literature:

With water; hydrogen bromide; In acetic acid; at 100 ℃; for 36h;

DOI:10.1021/ol500529w

Reference yield:

(2S,3S,4S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(1-formyl-2-phenylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (103314-30-3,103314-37-0,111563-58-7) → acromelic acid B (86630-10-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 98 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

2: 99 percent / DIBAH / hexane; toluene / 0.33 h / 0 °C

3: 98 percent / Na₂HPO₄, NaIO₄ / H₂O; methanol / 1 h / 40 °C

5: 87 percent / tetrahydrofuran; diethyl ether / 0.5 h / -15 °C

6: 83 percent / PDC / dimethylformamide / Ambient temperature

7: Na₂HPO₄, NaIO₄ / methanol; H₂O / 1 h / 40 °C

8: 1.) trifluoroacetic anhydride, pyridine 2.) 25percent aq. NH₃ / 1.) CH₂Cl₂, 0 deg C, 20 min; 2.) CH₂Cl₂, H₂O, r.t., overnight

9: selenium dioxide / pyridine / 100 °C

10: 2.) p-toluenesulfonic acid / 1.) MeOH, ether; 2.) MeOH, r.t., 30 min

11: 1.) PDC / 1.) DMF, 40 deg C, overnight; 2.) DMF, ether

12: 75 percent / mCPBa / CH₂Cl₂ / Ambient temperature

13: trifluoroacetic anhydride / dimethylformamide / Ambient temperature

14: 1.) 1 N KOH 2.) trifluoroacetic acid / 1.) MeOH, r.t., overnight; 2.) r.t., 30 min

With pyridine; potassium hydroxide; ammonium hydroxide; sodium periodate; disodium hydrogenphosphate; dipyridinium dichromate; selenium(IV) oxide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00222a044

Reference yield:

3-[(3S,4S,5S)-1-tert-Butoxycarbonyl-4-(2-hydroxy-ethyl)-5-hydroxymethyl-pyrrolidin-3-yl]-pyridine-2-carboxylic acid methyl ester → acromelic acid B (86630-10-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) PDC / 1.) DMF, 40 deg C, overnight; 2.) DMF, ether

2: 75 percent / mCPBa / CH₂Cl₂ / Ambient temperature

3: trifluoroacetic anhydride / dimethylformamide / Ambient temperature

4: 1.) 1 N KOH 2.) trifluoroacetic acid / 1.) MeOH, r.t., overnight; 2.) r.t., 30 min

With potassium hydroxide; dipyridinium dichromate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a044

upstream raw materials:

methyl (3S,4S,5S)-3-<1-(tert-butyloxycarbonyl)-4-<(methoxycarbonyl)methyl>-5-(methoxycarbonyl)-3-pyrrolidinyl>-1,6-dihydro-6-oxo-2-pyridinecarboxylate

(2S,3S,4S)-4-isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(-)-kainic acid

N-Boc-kainic acid

Refernces

• 1、 Ouchi, Hitoshi,Asahina, Aya,Asakawa, Tomohiro,Inai, Makoto,Hamashima, Yoshitaka,Kan, Toshiyuki. "Practical total syntheses of acromelic acids A and B". supporting information. p. 1980 - 1983. Retrieved 2014/05/06.
• 2、 Konno,Hashimoto,Ohfune,Shirahama,Matsumoto. "Acromelic acids A and B. Potent neuroexcitatory amino acids isolated from Clitocybe acromelalga". . p. 4807 - 4815. Retrieved 2007/10/02.