CID 115005

Base Information

• Chemical Name: CID 115005
• CAS No.: 265652-18-4
• Molecular Formula: C₁₅H₂₁N₅O₇S
• Molecular Weight: 415.427
• Nikkaji Number: J576.116F
• Wikidata: Q27160026
• Mol file: 265652-18-4.mol

Synonyms:(?)-7-epi-Cylindrospermopsin;Q27160026

Chemical Property of CID 115005

Chemical Property:

• XLogP3: -2.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 415.11616920
• Heavy Atom Count: 28
• Complexity: 867

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(CC2CC(NC3=NCC1N23)C(C4=CC(=O)NC(=O)N4)O)OS(=O)(=O)O
• Isomeric SMILES: C[C@H]1[C@H](C[C@@H]2C[C@@H](NC3=NC[C@H]1N23)[C@@H](C4=CC(=O)NC(=O)N4)O)OS(=O)(=O)O

Technology Process of CID 115005

There total 29 articles about CID 115005 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: 76.0%

C15H21N4(15)NO4*C2HF3O2 → cylindrospermopsin (265652-18-4,143545-90-8) + cylindrospermopsine (143545-90-8)

Guidance literature:

With sulfur trioxide pyridine complex; In N,N-dimethyl-formamide; at 0 - 23 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.8b03071

Reference yield: 63.0%

pyridine (110-86-1) + 6-[(S)-Hydroxy-((2aS,3R,4S,5aS,7R)-4-hydroxy-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triaza-acenaphthylen-7-yl)-methyl]-1H-pyrimidine-2,4-dione; hydrochloride → cylindrospermopsin (265652-18-4,143545-90-8) + Sulfuric acid mono-{(2aS,3R,4S,5aS,7R)-7-[(S)-(2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-sulfooxy-methyl]-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triaza-acenaphthylen-4-yl} ester; compound with pyridine

Guidance literature:

With sulfur trioxide; sodium sulfate; In N,N-dimethyl-formamide; at 24 ℃; for 0.5h;

DOI:10.1021/jo0486387

Reference yield: 59.0%

6-[(S)-Hydroxy-((2aS,3R,4S,5aS,7R)-4-hydroxy-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triaza-acenaphthylen-7-yl)-methyl]-1H-pyrimidine-2,4-dione; compound with trifluoro-acetic acid → cylindrospermopsin (265652-18-4,143545-90-8)

Guidance literature:

With pyridine-SO₃ complex; In N,N-dimethyl-formamide; for 1h;

DOI:10.1016/j.tet.2006.02.044

upstream raw materials:

pyridine

(3S,4R)-5-(4-bromobenzyloxy)-4-hydroxy-3-methylpent-1-ene

(3S,4S)-4-amino-5-(4-bromobenzyloxy)-3-methylpent-1-ene

(3S,4S)-5-(4-bromobenzyloxy)-4-hydroxylamino-3-methylpent-1-ene

Refernces

• 1、 Looper, Ryan E.,Runnegar, Maria T.C.,Williams, Robert M.. "Syntheses of the cylindrospermopsin alkaloids". . p. 4549 - 4562. Retrieved 2007/10/03.