159542-04-8

Basic information

• Product Name: hapalosin
• Synonyms: hapalosin
• CAS NO: 159542-04-8
• Molecular Formula: C28H43NO6
• Molecular Weight: 489.64412
• Mol File: 159542-04-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 689.2°Cat760mmHg
• Flash Point: 370.6°C
• Appearance: /
• Density: 1.057g/cm³
• Vapor Pressure: 6.06E-20mmHg at 25°C
• Refractive Index: 1.495
• PKA: 13.48±0.70(Predicted)
• CAS DataBase Reference: hapalosin(CAS DataBase Reference)
• NIST Chemistry Reference: hapalosin(159542-04-8)
• EPA Substance Registry System: hapalosin(159542-04-8)

Safety Data

• Hazardous Substances Data: 159542-04-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C28H43NO6/c1-6-7-8-9-13-16-24-20(4)28(33)35-26(19(2)3)27(32)29(5)22(23(30)18-25(31)34-24)17-21-14-11-10-12-15-21/h10-12,14-15,19-20,22-24,26,30H,6-9,13,16-18H2,1-5H3/t20-,22-,23+,24+,26-/m0/s1

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Relevant articles and documents

An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (?)-hapalosin

A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.

A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization

A practical total synthesis of hapalosin, a compound with multidrug resistance-reversing activity, has been carried out using an unprecedented macrolactonization strategy. One of the features of the new approach is the straightforward and fully stereocont

Synthesis and evaluation of hapalosin and analogs as MDR-reversing agents

The marine natural product hapalosin and 22 analogs, which incorporated systematic substituent deletions or variations, were prepared. These compounds were evaluated in a cell-based assay for both MDR-reversing activity and general cytotoxicity. Some substituent modifications resulted in lower cytotoxicities, but most structural changes were either detrimental to or did not seriously alter the MDR-reversing activity.