23498-36-4

Basic information

• Product Name: (1S,3Z,5E,7S,9Z,11Z,13S,15R,19R)-7-hydroxy-2-{[(2R)-2-hydroxypropanoyl]amino}-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-13-yl acetate
• CAS NO: 23498-36-4
• Molecular Formula: C₂₇H₃₇NO₈
• Molecular Weight: 503.5846
• Mol File: 23498-36-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 737.3°C at 760 mmHg
• Flash Point: 399.7°C
• Density: 1.22g/cm³
• Vapor Pressure: 4.31E-25mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: (1S,3Z,5E,7S,9Z,11Z,13S,15R,19R)-7-hydroxy-2-{[(2R)-2-hydroxypropanoyl]amino}-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-13-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3Z,5E,7S,9Z,11Z,13S,15R,19R)-7-hydroxy-2-{[(2R)-2-hydroxypropanoyl]amino}-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-13-yl acetate(23498-36-4)
• EPA Substance Registry System: (1S,3Z,5E,7S,9Z,11Z,13S,15R,19R)-7-hydroxy-2-{[(2R)-2-hydroxypropanoyl]amino}-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-13-yl acetate(23498-36-4)

Safety Data

• Hazardous Substances Data: 23498-36-4(Hazardous Substances Data)

Relevant articles and documents

Landscape of Lankacidin Biomimetic Synthesis: Structural Revisions and Biogenetic Implications

In this report, a unified biomimetic approach to all known macrocyclic lankacidins is presented. By taking advantage of the thermolysis of N,O-acetal to generate the requisite N-acyl-1-azahexatriene species, we eventually realized the biomimetic Mannich macrocyclization, from which all of the macrocyclic lankacidins can be conquered by orchestrated desilylation. The reassignments of the reported structures of isolankacidinol (7 to 10) and the discovery of a recently isolated lankacyclinol found to be in fact 2,18-bis-epi-lankacyclinol (72) unraveled the previously underappreciated chemical diversity exhibited by the enzymatic macrocyclization. In addition, the facile elimination/decarboxylation/protonation process for the depletion of C1 under basic conditions resembling a physiological environment may implicate more undiscovered natural products with variable C2/C18 stereochemistries (i.e., 62, 73, and 75). The notable aspect provided by a biomimetic strategy is significantly reducing the step count compared with the two previous entries to macrocyclic lankacidins.