185138-92-5

Basic information

• Product Name: Taurospongin A
• Synonyms: Taurospongin A
• CAS NO: 185138-92-5
• Molecular Formula: C40H71NO9S
• Molecular Weight: 742.058
• Mol File: 185138-92-5.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.066g/cm³
• Refractive Index: 1.499
• CAS DataBase Reference: Taurospongin A(CAS DataBase Reference)
• NIST Chemistry Reference: Taurospongin A(185138-92-5)
• EPA Substance Registry System: Taurospongin A(185138-92-5)

Safety Data

• Hazardous Substances Data: 185138-92-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C41H73NO8S/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-29-40(45)50-37(3)34-38(33-36(2)43)28-27-30-41(4,46)35-39(44)42-31-32-51(47,48)49/h20-21,37-38,46H,5-19,22-23,26-35H2,1-4H3,(H,42,44)(H,47,48,49)/b21-20-/t37-,38-,41-/m1/s1

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Relevant articles and documents

Taurospongins B and C, new acetylenic fatty acid derivatives possessing a taurine amide residue from a marine sponge of the family Spongiidae

Two new acetylenic fatty acid derivatives possessing a taurine amide residue, taurospongins B (1) and C (2), have been isolated from an Okinawan marine sponge of the family Spongiidae. The gross structures of 1 and 2 were elucidated on the basis of their spectral data, especially 2D NMR and FABMS/MS data. The absolute configurations for 1 and 2 were established by chemical means. Taurospongin C (2) showed inhibitory activity against Cryptococcus neoformans.

Synthesis of taurospongin A

(Figure presented) Two new routes to the C(1-10) carboxylic acid core of taurospongin A are presented. In the first route, overall asymmetric hydration of a C(2)-C(3) alkene is achieved by Sharpless AD and selective deoxygenation at C(2); in the second route, the C(3) stereogenic center is set by Tietze asymmetric allylation. A short synthesis of the C(1′-25′) fatty acid combines with the product from the first route to complete the total synthesis of taurospongin A.

Use of π-allyltricarbonyliron lactone complexes in the synthesis of taurospongin A: A potent inhibitor of DNA polymerase β and HIV reverse transcriptase

The total synthesis of taurospongin A by two new approaches has been achieved where π-allyltricarbonyliron lactone complexes have been used to control highly stereoselective additions of the nucleophiles to a carbonyl unit located in the side chain of the

Synthesis of taurospongin A: a potent inhibitor of DNA polymerase and HIV reverse transcriptase, using pi-allyltricarbonyliron lactone complexes.

The synthesis of taurospongin A has been achieved using, as a key step, a pi-allyltricarbonyliron lactone complex to control a highly stereoselective addition of a methyl group to a carbonyl unit located in the side chain of the complex.