136266-35-8

Basic information

• Product Name: cinatrin C1
• Synonyms: cinatrin C1
• CAS NO: 136266-35-8
• Molecular Formula: C18H30O8
• Molecular Weight: 374.427
• Mol File: 136266-35-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 528°Cat760mmHg
• Flash Point: 181.2°C
• Appearance: /
• Density: 1.203g/cm³
• Vapor Pressure: 2.36E-13mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: cinatrin C1(CAS DataBase Reference)
• NIST Chemistry Reference: cinatrin C1(136266-35-8)
• EPA Substance Registry System: cinatrin C1(136266-35-8)

Safety Data

• Hazardous Substances Data: 136266-35-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H30O8/c1-2-3-4-5-6-7-8-9-10-11-12-24-18(22)15-13(16(20)26-23)14(19)17(21)25-15/h13-15,19,23H,2-12H2,1H3/t13-,14-,15+/m1/s1

Upstream product

• 193957-74-3 benzyl-(3R,4S,5S)-2-oxo-3,4-dihydroxy-4-carboxy-5-dodecyl-tetrahydrofuran-5-carboxylate 
• 31161-71-4 benzyl Myristate 
• 193957-71-0 benzyl-2-oxo-tetradecanoate 
• 193957-70-9 benzyl-2-hydroxytetradecanoate 
• 136266-39-2 cinatrin C₁ dimethyl ester 
• 404935-56-4 (2R,3S,4S,5S)-3,4-Bis-benzyloxy-2-((E)-dodec-2-enyl)-5-methoxy-tetrahydro-furan-2-carboxylic acid methyl ester 
• 641610-04-0 methyl methyl-4-C-dodecanyl-D-erythro-3-pentulofuranosiduronate 
• 1429481-14-0 tert-butyl (4aS,6R,7R,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-6-(hydroxymethyl)-2,2-dimethyl-4H-furo[3,2-d][1,3]-dioxine-7a-carboxylate 
• 1429481-15-1 C₃₃H₅₂O₈ 
• 1429481-16-2 tert-butyl (4aS,7S,7aS)-7-(benzyloxy)-4a-dodecyltetrahydro-2,2-dimethyl-6-oxo-4H-furo[3,2-d][1,3]dioxine-7a-carboxylate 
• 1429481-05-9 (2R,3R,3aS,6aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-tetrahydro-3a-hydroxy-6a-(hydroxymethyl)furo[3,4-b]furan-6-(6aH)-one 
• 1429481-07-1 7-(benzyloxy)-6-((benzyloxy)methyl)-2,2-dimethyldihydro-4H-4a,7a-(methanooxymethano)furo[3,2-d]-[1,3]dioxin-10-one 
• 124-10-7 methyl myristoate 

Relevant articles and documents

Enantiospecific synthesis of the phospholipase A2 inhibitors (-)-cinatrin C1 and (+)-cinatrin C3

The enantiospecific synthesis of (-)-cinatrin C1 (3) and (-)-cinatrin C3 (5) from the D-arabinose derivative 9 is described. The stereochemistry at C2 was introduced via a chelation-controlled addition of a carbanion to a-hydroxy ketone 8. The best selectivity was achieved by use of the Grignard reagent derived from trimethylsilylacetylene. Transformation of the terminal alkyne into methyl ester 17 followed by acetal hydrolysis and selective lactol oxidation gave cinatrin C1 dimethyl ester (7). Base hydrolysis and acid induced relactonization then gave a 1 : 1 mixture of cinatrins C1 (3) and C3 (5).

METHOD FOR OBTAINING CINATRINS C3 AND C1

The present invention relates to a process for obtaining cinatrins C1 and C3 and derivatives thereof which comprises the hydroxylation of a compound of formula (III). The invention also relates to the intermediates of said synthesis