1053480-87-7

Basic information

• Product Name: (2R,3S,4S,5S)-3,4-Bis-benzyloxy-2-((E)-dodec-2-enyl)-5-methoxy-tetrahydro-furan-2-carboxylic acid
• CAS NO: 1053480-87-7
• Molecular Weight: 524.698
• Mol File: 1053480-87-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,5S)-3,4-Bis-benzyloxy-2-((E)-dodec-2-enyl)-5-methoxy-tetrahydro-furan-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,5S)-3,4-Bis-benzyloxy-2-((E)-dodec-2-enyl)-5-methoxy-tetrahydro-furan-2-carboxylic acid(1053480-87-7)
• EPA Substance Registry System: (2R,3S,4S,5S)-3,4-Bis-benzyloxy-2-((E)-dodec-2-enyl)-5-methoxy-tetrahydro-furan-2-carboxylic acid(1053480-87-7)

Safety Data

• Hazardous Substances Data: 1053480-87-7(Hazardous Substances Data)

Upstream product

• 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 

Downstream Products

• 136266-34-7 (-)-cinatrin B 
• 404935-61-1 (2S,3S,4S,5R,8S)-3,4-Bis-benzyloxy-8-decyl-2-methoxy-1,7-dioxa-spiro[4.4]nonan-6-one 
• 404935-60-0 (2S,3S,4S,5R,8R)-3,4-Bis-benzyloxy-8-((R)-1-iodo-decyl)-2-methoxy-1,7-dioxa-spiro[4.4]nonan-6-one 

Relevant articles and documents

Enantiospecific synthesis of the phospholipase A2 inhibitor (-)-cinatrin B

The first enantiospecific synthesis of phospholipase A2 (PLA2) inhibitor (-)-cinatrin B (2) from the D-arabinose derivative 9 is described. The spirolactone system was formed by an Ireland-Claisen rearrangement of the allyl ester 8 followed by hydrolysis and stereoselective iodolactonization. The stereoselectivity of the rearrangement was controlled by the asymmetry in the allylic alcohol fragment. Ester (S)-8 gave the desired rearrangement product 7 and the epimer 13 in high yield as a 73:27 ratio, respectively. The final stereocenter at C2 was introduced via a chelation-controlled addition of the Grignard reagent derived from trimethylsilylacetylene to α-hydroxy ketone 6. Transformation of the terminal alkyne into the methyl ester 21 followed by acetal hydrolysis and selective lactol oxidation afforded cinatrin B methyl ester (22). Base hydrolysis and acid-induced relactonization then gave (-)-cinatrin B (2).