Azaspiracid1

Base Information

• Chemical Name: Azaspiracid1
• CAS No.: 214899-21-5
• Molecular Formula: C47H71NO12
• Molecular Weight: 842.08
• DSSTox Substance ID: DTXSID9040974
• Metabolomics Workbench ID: 181383
• Nikkaji Number: J2.290.668B
• Mol file: 214899-21-5.mol

Synonyms:AZASPIRACID1;Azaspiracid 1;DTXSID9040974

Chemical Property of Azaspiracid1

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.27g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 9
• Exact Mass: 841.49762670
• Heavy Atom Count: 60
• Complexity: 1690

Purity/Quality:

98%Min ^*data from raw suppliers

AZASPIRACID-1 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison by ingestion.
• Hazard Codes: A poison by ingestion.

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2C3C(CC4(O3)C(CC(CN4)C)C)OC(C1)(O2)CC(=C)C5C(CC(C(O5)(C(C6CC7C(O6)CC(C8(O7)CCC9(O8)CC=CC(O9)C=CCCC(=O)O)C)O)O)C)C
• Isomeric SMILES: C[C@H]1C[C@@H]2[C@@H]3[C@@H](C[C@]4(O3)[C@H](C[C@H](CN4)C)C)O[C@](C1)(O2)CC(=C)[C@@H]5[C@H](C[C@H]([C@@](O5)([C@@H]([C@@H]6C[C@@H]7[C@H](O6)C[C@H]([C@@]8(O7)CC[C@@]9(O8)CC=C[C@H](O9)/C=C/CCC(=O)O)C)O)O)C)C

Technology Process of Azaspiracid1

There total 59 articles about Azaspiracid1 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: 90.0%

C47H71NO11 → (+)-azaspiracid (214899-21-5)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol;

DOI:10.1002/anie.200701520

Reference yield: 60.0%

C65H111NO14Si3 (782479-30-5) → azaspiracid-1 (214899-21-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 15h;

DOI:10.1002/anie.200460696

Reference yield: 55.0%

C65H111NO14Si3 (881652-02-4) → C1-C20-epimerof azaspiracid-1 (214899-21-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 15h;

DOI:10.1021/ja054750q

upstream raw materials:

C₆₅H₁₁₁NO₁₄Si₃

C₂₆H₃₈O₇

C₂₆H₄₀O₇

C₂₆H₃₈O₈

Refernces

• 1、 Evans, David A.,Dunn, Travis B.,Kvaerno, Lisbet,Beauchemin, Andre,Raymer, Brian,Olhava, Edward J.,Mulder, Jason A.,Juhl, Martin,Kagechika, Katsuji,Favor, David A.. "Total synthesis of (+)-azaspiracid-1. Part II: Synthesis of the EFGHI sulfone and completion of the synthesis". . p. 4698 - 4703. Retrieved 2008/02/10.
• 2、 Nicolaou,Koftis, Theocharis V.,Vyskocil, Stepan,Petrovic, Goran,Ling, Taotao,Yamada, Yoichi M. A.,Tang, Wenjun,Frederick, Michael O.. "Structural revision and total synthesis of azaspiracid-1, part 2: Definition of the ABCD domain and total synthesis". . p. 4318 - 4324. Retrieved 2007/10/03.