CID 3425471

Base Information

• Chemical Name: CID 3425471
• CAS No.: 109946-35-2
• Molecular Formula: C₄₁H₆₆O₁₃
• Molecular Weight: 766.967
• European Community (EC) Number: 620-961-5
• Nikkaji Number: J474.550G
• Wikipedia: Tautomycin
• Mol file: 109946-35-2.mol

Synonyms:tautomycin

Chemical Property of CID 3425471

Chemical Property:

• Vapor Pressure: 5.62E-34mmHg at 25°C
• Boiling Point: 854.3°Cat760mmHg
• PKA: 12.33±0.20(Predicted)
• Flash Point: 247.5°C
• PSA: 192.19000
• Density: 1.18g/cm³
• LogP: 4.78530
• Storage Temp.: −20°C
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 21
• Exact Mass: 766.45034216
• Heavy Atom Count: 54
• Complexity: 1360

Purity/Quality:

98%min ^*data from raw suppliers

Tautomycin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 22-28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC2(CCC(C(O2)C(C)CCC(C(C)C(=O)CC(C(C(C(C)C)OC(=O)CC(C3=C(C(=O)OC3=O)C)O)OC)O)O)C)OC1CCC(C)C(=O)C
• General Description: Tautomycin is a biologically active secondary metabolite known for its role as a serine/threonine phosphatase inhibitor, with potential therapeutic applications. The successful synthesis of its C1-C21 fragment demonstrates progress toward accessing this complex natural product, highlighting its structural intricacy and the importance of stereoselective methods in its preparation. This advancement paves the way for further research into tautomycin’s biological mechanisms and drug development.

Technology Process of CID 3425471

There total 139 articles about CID 3425471 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: 84.0%

tris-O-(tert-butyldimethylsilyl)tautomycin (170708-67-5) → tautomycin (109946-35-2)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4020(97)00228-7

Reference yield: 82.0%

C55H80O14 (1054656-75-5) → tautomycin (109946-35-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; water; for 0.0833333h;

DOI:10.1021/jo961633s

Reference yield: 77.0%

18,22,3'-Tris-O-(triethylsilyl)tautomycin (165961-34-2) → tautomycin (109946-35-2)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 3 ℃; for 1h;

DOI:10.1021/jo00121a026

upstream raw materials:

Ethyl <2Z,4R,8R,9S,10R,13S,14S,17R,17<2S,3S,6R,8S,8(3S),9R>>-4,10,14-trihydroxy-9-methoxy-2,13,17-trimethyl-3-<(1,1-dimethylethoxy)carbonyl>-8-(1-methylethyl)-17-<3,9-dimethyl-8-(3-methyl-4-oxopentyl)-1,7-dioxaspiro<5.5>undec-2-yl>-6,12-dioxo-7-oxa...

18,22,3'-Tris-O-(triethylsilyl)tautomycin

tris-O-(tert-butyldimethylsilyl)tautomycin

C₅₅H₈₀O₁₄

Refernces

Synthesis of the C1-C21 fragment of the serine/threonine phosphatase inhibitor tautomycin

10.1021/jo952083l

The research focuses on the synthesis of the C1-C21 fragment of the serine/threonine phosphatase inhibitor tautomycin, a novel secondary metabolite with significant biological activity. The purpose of this study was to develop a synthetic route to this complex natural product, which could potentially lead to the development of new therapeutic agents. The researchers successfully synthesized compound 40, which contains the C1-C21 region of tautomycin, using a series of chemical reactions that included the Matteson’s chloromethylene insertion reaction to construct stereocenters and Cr/Ni-mediated coupling to form the spirocyclic structure. Key chemicals used in the synthesis process included various organometallic reagents, protecting groups like PMB (para-methoxybenzyl), and reagents for oxidation and reduction steps such as DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) and lithium aluminum hydride. The conclusions of the research detailed the successful synthesis of the target fragment with a high degree of stereoselectivity, setting the stage for further extension to the natural product tautomycin and potential applications in the study of serine/threonine phosphatases.