Ascomycin

Base Information

• Chemical Name: Ascomycin
• CAS No.: 104987-12-4
• Deprecated CAS: 11011-38-4,159430-76-9,126340-36-1,133876-12-7,137767-75-0,148400-02-6
• Molecular Formula: C₄₃H₆₉NO₁₂
• Molecular Weight: 792.02
• Hs Code.: 29419090
• European Community (EC) Number: 435-850-5,600-627-5,658-052-0
• UNII: AUF4U5NSJK
• ChEMBL ID: CHEMBL8597
• DSSTox Substance ID: DTXSID80894126
• Metabolomics Workbench ID: 144422
• Nikkaji Number: J476.843D
• Pharos Ligand ID: FV1S8MSZLMSZ
• Wikidata: Q4803998
• Wikipedia: Ascomycin
• Mol file: 104987-12-4.mol

Synonyms:ascomycin;changchuanmycin;FK 520;FK-520;FR 900520;FR-900520;immunomycin;tacrolimus related compound A

Chemical Property of Ascomycin

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 153-157 °C
• Refractive Index: 1.543
• Boiling Point: 868.3 °C at 760 mmHg
• PKA: 9.97±0.70(Predicted)
• Flash Point: 478.9 °C
• PSA: 178.36000
• Density: 1.19 g/cm³
• LogP: 4.41080
• Storage Temp.: −20°C
• Solubility.: ≥38.9 mg/mL in DMSO; insoluble in H2O; ≥98.6 mg/mL in EtOH
• Water Solubility.: Soluble in DMSO at 65mg/ml; soluble in ethanol at 50mg/m; with warming. Very poorly soluble in water
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 791.48197664
• Heavy Atom Count: 56
• Complexity: 1430

Purity/Quality:

99% ^*data from raw suppliers

Ascomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,F
• Statements: 20/21/22-36-11
• Safety Statements: 36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC)C)C
• Isomeric SMILES: CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC)C)\C
• Uses: A potent immunosuppressive agent and could be used as a potential therapeutic agent for autoimmune diseases Ascomycin is a macrocyclic lactone closely related to tacrolimus and rapamycin. Ascomycin is isolated from several species of Streptomyces and was first reported in 1988. Ascomycin exhibits limited, potent antifungal activity but has found considerable utility as an immunosuppressant. Everolimus is a semi-synthetic macrocyclic lactone prepared from rapamycin by selective alkylation of the 42-hydroxy group with a silyl-protected hydroxyethyl triflate moiety, followed by addition of an ethylhydroxy moiety to provide greater stability and bioavailability. Like all tacrolimus analogues, everolimus binds to receptor protein, FKBP12. The complex then binds to mTOR preventing it from interacting with target proteins. Everolimus is extensively cited in the literature with over 2,000 citations.

Technology Process of Ascomycin

There total 10 articles about Ascomycin 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: 56.0%

→ ascomycin (135635-46-0,137767-76-1,104987-12-4,133876-12-7)

Guidance literature:

Purification / work up;

Reference yield:

11-epi-ascomycin (671222-63-2,133876-12-7) → ascomycin (135635-46-0,137767-76-1,104987-12-4,133876-12-7)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tetlet.2003.10.199

Reference yield:

24,33-bis-OTBDMS-ascomycin (137071-45-5) → ascomycin (135635-46-0,137767-76-1,104987-12-4,133876-12-7)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 2.5h;

DOI:10.1002/jlcr.558

upstream raw materials:

24,33-bis-OTBDMS-ascomycin

11-epi-ascomycin

2(R),10(S),11(S)-cyclo-ascomycin

C₆₁H₁₁₃NO₁₂Si₃

Downstream raw materials:

C₄₃H₆₉NO₁₂

L 685818

17-but-1-enyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-21,23-dimethoxy-13,17,19,25-tetramethyl-11,26-dioxa-4-aza-tricyclo[20.3.1.0^4,9]hexacosane-2,3,10,16-tetraone

4-β-methoxy-9-dihydroascomycin

Refernces

• 1、 -. "A PROCESS FOR THE RECOVERY OF SUBSTANTIALLY PURE TRICYCLIC MACROLIDE". Page/Page column 9-10. . Retrieved 2008/06/13.
• 2、 Baumann, Karl,Bacher, Markus,Damont, Annelaure,Steck, Andrea. "Selective transformation of ascomycin into 11-epi-ascomycin". . p. 549 - 551. Retrieved 2007/10/03.