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Streptovaricin U

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Category Others
Catalog number BBF-03074
CAS 74200-47-8
Molecular Weight 655.77
Molecular Formula C36H49NO10

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Fermentation Lab

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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

Streptovaricin U is an acyclic ansamycin produced by Str. spectabilis.

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IUPAC Name (2E,4S,5S,6R,7R,8R,9R,10R,11R,12R,13Z,15E)-5,7,9,11-tetrahydroxy-17-[(6-hydroxy-3,7-dimethyl-1,4-dioxonaphthalen-2-yl)amino]-2,4,6,8,10,12,16-heptamethyl-17-oxoheptadeca-2,13,15-trienoic acid
Canonical SMILES CC1=CC2=C(C=C1O)C(=O)C(=C(C2=O)NC(=O)C(=CC=CC(C)C(C(C)C(C(C)C(C(C)C(C(C)C=C(C)C(=O)O)O)O)O)O)C)C
InChI InChI=1S/C36H49NO10/c1-16(29(39)22(7)31(41)24(9)32(42)23(8)30(40)19(4)13-20(5)36(46)47)11-10-12-17(2)35(45)37-28-21(6)33(43)26-15-27(38)18(3)14-25(26)34(28)44/h10-16,19,22-24,29-32,38-42H,1-9H3,(H,37,45)(H,46,47)/b11-10-,17-12+,20-13+/t16-,19+,22-,23-,24-,29-,30+,31-,32-/m1/s1
InChI Key IWYUWDJCRPTLOZ-UIZAHVQOSA-N
Appearance Orange Powder
Boiling Point 937.0±65.0°C at 760 mmHg
Melting Point 115-140°C
Density 1.3±0.1 g/cm3
1. Stereoselective synthesis of macrolide-type antibiotics from epoxy amides. Synthesis of the polypropionate chain of streptovaricin u
Francisco Sarabia, Antonio Sánchez-Ruiz, Laura Martín-Ortiz, Miguel García-Castro, Samy Chammaa Org Lett. 2007 Nov 22;9(24):5091-4. doi: 10.1021/ol7022938. Epub 2007 Nov 2.
The synthesis of the polypropionate chain of Streptovaricin U (1) is described utilizing a new approach for the stereoselective synthesis of the macrolide-type antibiotics via sulfur ylides.
2. Stereoselective construction of all-anti polypropionate modules: synthesis of the C5-C10 fragment of streptovaricin U
Wildeliz Torres, Raúl R Rodríguez, José A Prieto J Org Chem. 2009 Mar 20;74(6):2447-51. doi: 10.1021/jo8026966.
A concise nonaldol approach for the stereoselective construction of all-anti polypropionate fragments was developed. The iterative epoxide-based methodology consists of the syn-selective epoxidation of cis homoallylic alcohols with use of the VO(acac)(2)-catalyzed conditions followed by epoxide cleavage with a propynyl aluminum reagent as key steps. The methodology was applied to the synthesis of the all-anti C6-C10 fragment of streptovaricin U.

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