141205-31-4

Basic information

• Product Name: microcolin A
• Synonyms: microcolin A
• CAS NO: 141205-31-4
• Molecular Formula: C39H65N5O9
• Molecular Weight: 747.969
• Mol File: 141205-31-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 862.5°Cat760mmHg
• Flash Point: 475.4°C
• Appearance: /
• Density: 1.147g/cm³
• Vapor Pressure: 1.1E-34mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: microcolin A(CAS DataBase Reference)
• NIST Chemistry Reference: microcolin A(141205-31-4)
• EPA Substance Registry System: microcolin A(141205-31-4)

Safety Data

• Hazardous Substances Data: 141205-31-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C39H65N5O9/c1-13-14-15-24(6)19-25(7)37(50)41(11)30(18-22(2)3)35(48)40-36(49)34(27(9)53-28(10)45)42(12)33(23(4)5)39(52)43-21-29(46)20-31(43)38(51)44-26(8)16-17-32(44)47/h16-17,22-27,29-31,33-34,46H,13-15,18-21H2,1-12H3,(H,40,48,49)/t24-,25-,26+,27-,29+,30+,31+,33+,34+/m1/s1

Upstream product

• 618-27-9 hydroxy L-proline 
• 177767-31-6 (3(2R,4R)4S)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone 
• 359862-15-0 (2R',4R)-3-(2-methylhexanoyl)-4-benzyl-2-oxazolidinone 
• 177607-72-6 Trifluoro-methanesulfonic acid (R)-2-methyl-hexyl ester 
• 177607-75-9 (S)-2-({(2S,3R)-3-Acetoxy-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-butyryl}-methyl-amino)-3-methyl-butyric acid benzyl ester 
• 177607-79-3 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-2-hydroxy-1-methyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1053609-48-5 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-3-methanesulfonyloxy-2-methyl-5-oxo-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 177607-76-0 (S)-2-({(2S,3R)-3-Acetoxy-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-4-methyl-pentanoylamino]-butyryl}-methyl-amino)-3-methyl-butyric acid 
• 177607-78-2 (2S,4S)-2-((S)-1-Benzyloxycarbonyl-ethylcarbamoyl)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 177607-73-7 (S)-2-[((2S,3R)-3-Acetoxy-2-tert-butoxycarbonylamino-butyryl)-methyl-amino]-3-methyl-butyric acid benzyl ester 
• 177607-80-6 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-3-hydroxy-2-methyl-5-oxo-2,5-dihydro-pyrrole-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 177607-77-1 (2S,4S)-2-((S)-1-Benzyloxycarbonyl-ethylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 177607-89-5 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 177607-90-8 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-2-methyl-5-oxo-2,5-dihydro-pyrrole-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Total asymmetric synthesis of the potent immunosuppressive marine natural product microcolin A

The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported. The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.