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Sch 725674

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Sch 725674
Category Enzyme inhibitors
Catalog number BBF-04288
CAS 877061-66-0
Molecular Weight 328.44
Molecular Formula C18H32O5
Purity >95% by HPLC

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is a macrocyclic lactone structurally related to gloeosporone. It is a self-germination inhibitor produced by colletotrichum gloeosporioides. It exhibits moderate antifungal activity.

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Synonyms Antibiotic Sch 725674; (3E,5R,6S,8R,14R)-5,6,8-Trihydroxy-14-pentyloxacyclotetradec-3-en-2-one; Sch-725674; 5R,6S,8R-trihydroxy-14R-pentyl-oxacyclotetradec-3E-en-2-one
Storage Store at -20°C
IUPAC Name (3E,5R,6S,8R,14R)-5,6,8-trihydroxy-14-pentyl-1-oxacyclotetradec-3-en-2-one
Canonical SMILES CCCCCC1CCCCCC(CC(C(C=CC(=O)O1)O)O)O
InChI InChI=1S/C18H32O5/c1-2-3-5-9-15-10-7-4-6-8-14(19)13-17(21)16(20)11-12-18(22)23-15/h11-12,14-17,19-21H,2-10,13H2,1H3/b12-11+/t14-,15-,16-,17+/m1/s1
InChI Key LEEBEEPDVOWSDN-CDBVEKOQSA-N
Source Colletotrichum sp.
Appearance White Solid
Antibiotic Activity Spectrum Fungi
Boiling Point 525.7±50.0°C at 760 mmHg
Density 1.1±0.1 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO
1. First Total Synthesis of Gliomasolide C and Formal Total Synthesis of Sch-725674
B Seetharamsingh, D Srinivasa Reddy, Pankaj V Khairnar J Org Chem . 2016 Jan 4;81(1):290-6. doi: 10.1021/acs.joc.5b02318.
Syntheses of two 14-membered macrolides Sch-725674 and Gliomasolide C are described here. The first total synthesis of Gliomasolide C, the short synthesis of Sch-725674, and regioselective Wacker oxidation of internal olefin are the highlights of this disclosure. In addition, a key macrocycle with orthogonal functionalities was designed and synthesized on a gram scale for the generation of analogues.
2. Structure elucidation of Sch 725674 from Aspergillus sp
Mahesh Patel, Shu-Wei Yang, Joseph Terracciano, Tze-Ming Chan, Min Chu, David Loebenberg J Antibiot (Tokyo) . 2005 Aug;58(8):535-8. doi: 10.1038/ja.2005.74.
A new macrolide Sch725674 (1) was isolated and identified from the culture of an Aspergillus sp. The structure elucidation of 1 was accomplished based on extensive NMR spectroscopic analyses. Compound 1 showed inhibitory activity against Saccharomyces cerevisiae (PM503) and Candida albicans (C43) with MICs of 8 and 32 microg/ml, respectively.
3. Enantiospecific total synthesis of macrolactone Sch 725674
Kavirayani R Prasad, Sunil K Sunnam, Amit K Bali Org Lett . 2014 Aug 1;16(15):4001-3. doi: 10.1021/ol5018678.
The enantiospecific total synthesis of 14-membered macrolactone Sch 725674 was accomplished from tartaric acid. Key reactions in the synthesis include the Ley's dithiaketalization of an alkynone derived from the bis-Weinreb amide of tartaric acid, Boord olefination, and ring-closing metathesis of an acrylate ester.

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