AAL Toxin TA1

Base Information

• Chemical Name: AAL Toxin TA1
• CAS No.: 79367-52-5
• Molecular Formula: C₂₅H₄₇NO₁₀
• Molecular Weight: 521.649
• Nikkaji Number: J3.139.521F
• Wikidata: Q110172685
• Metabolomics Workbench ID: 164969
• Mol file: 79367-52-5.mol

Synonyms:AAL Toxin TA1;(2R)-2-[2-[(3R,4R,5S,7S,13R,14S,16S)-17-Amino-4,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-5-yl]oxy-2-oxoethyl]butanedioic acid;79367-52-5;Alternaria alternata Toxin TA1

Chemical Property of AAL Toxin TA1

Chemical Property:

• Vapor Pressure: 5.9E-25mmHg at 25°C
• Boiling Point: 735.3°C at 760 mmHg
• Flash Point: 398.5°C
• Density: 1.235g/cm³
• XLogP3: -1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 22
• Exact Mass: 521.31999670
• Heavy Atom Count: 36
• Complexity: 646

Purity/Quality:

99% ^*data from raw suppliers

AALToxinTA1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)C(C(CC(C)CCCCCC(C(CC(CN)O)O)O)OC(=O)CC(CC(=O)O)C(=O)O)O
• Isomeric SMILES: CC[C@@H](C)[C@H]([C@H](C[C@@H](C)CCCCC[C@H]([C@H](C[C@@H](CN)O)O)O)OC(=O)C[C@@H](CC(=O)O)C(=O)O)O

Technology Process of AAL Toxin TA1

There total 25 articles about AAL Toxin TA1 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:

(R)-3-Carboxy-pentanedioic acid mono-[(1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl] ester (251353-67-0) → AAL-toxin TA1 (79367-52-5)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)01322-2

Reference yield:

(S)-5-((1R,2R)-1-Hydroxy-2-methyl-butyl)-dihydro-furan-2-one (182370-51-0) → AAL-toxin TA1 (79367-52-5)

Guidance literature:

Multi-step reaction with 12 steps

1: TfOH / CH₂Cl₂; cyclohexane

2: 68 percent / LiHMDS / tetrahydrofuran / -78 °C

3: 72 percent / n-BuLi / diethyl ether / -20 °C

4: 85 percent / NaBH₄; CeCl₃ / methanol

5: 97 percent / Ac₂O; Py

6: 84 percent / Pd(OAc)2; n-Bu₃P / tetrahydrofuran

7: LiAlH₄ / tetrahydrofuran

8: PPTS / ethanol

9: 69 percent / HN₃; Ph₃P; DEAD / toluene

10: DMAP / toluene

11: TBAF / tetrahydrofuran

12: H₂; 1M HCl / Pd-C / 2-methyl-propan-2-ol; tetrahydrofuran

With pyridine; hydrogenchloride; dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; tributylphosphine; tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; acetic anhydride; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; toluene; tert-butyl alcohol; 1: Etherification / 2: Alkylation / 3: Acylation / 4: Reduction / 5: Esterification / 6: deoxygenation / 7: Reduction / 8: ether cleavage / 9: Alkylation / 10: Acylation / 11: ester cleavage / 12: Hydrogenolysis;

DOI:10.1016/S0040-4039(99)01322-2

Reference yield:

(S)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid mono-(2-trimethylsilanyl-ethyl) ester (182247-16-1) → AAL-toxin TA1 (79367-52-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / toluene

2: DMAP / toluene

3: TBAF / tetrahydrofuran

4: H₂; 1M HCl / Pd-C / 2-methyl-propan-2-ol; tetrahydrofuran

With hydrogenchloride; dmap; tetrabutyl ammonium fluoride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; toluene; tert-butyl alcohol; 1: Acylation / 2: Acylation / 3: ester cleavage / 4: Hydrogenolysis;

DOI:10.1016/S0040-4039(99)01322-2

upstream raw materials:

(R)-3-Carboxy-pentanedioic acid mono-[(1S,3S,9R,10S,12S)-13-azido-9,10,12-tris-benzyloxy-1-((1R,2R)-1-benzyloxy-2-methyl-butyl)-3-methyl-tridec-5-ynyl] ester

(S)-5-((1R,2R)-1-Hydroxy-2-methyl-butyl)-dihydro-furan-2-one

(S)-3-(2-Trimethylsilanyl-ethoxycarbonyl)-pentanedioic acid mono-(2-trimethylsilanyl-ethyl) ester

(S)-5-((1R,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-dihydro-furan-2-one