76745-19-2

Upstream product

• 78606-79-8 Benzoic acid (S)-4-methoxycarbonyl-1-(R)-oxiranyl-butyl ester 
• 79356-62-0 (5R,6R)-epoxy-7-hydroxyheptanoic acid methyl ester 
• 65-85-0 benzoic acid 
• 148407-21-0 (5R,6R)-methyl 7-(p-nitrobenzoyloxy)-5,6-epoxyheptanoate 
• 533-67-5 2-Deoxy-D-ribose 
• 78606-80-1 5(S), 6(R), 7-trihydroxyheptanoic acid methyl ester 
• 78606-78-7 methyl (E,5S,6R)-5,6,7-trihydroxyhept-2-enoate 
• 76745-17-0 (5S,6R)-5,6-Dihydroxy-7-(toluene-4-sulfonyloxy)-heptanoic acid methyl ester 
• 76871-77-7 cis-7-hydroxy-5-heptenoic acid,methyl ester 
• 111037-30-0 (5S,6R)-Methyl 5-(benzyloxy)-6,7-O-isopropylideneheptanoate 

Downstream Products

• 111037-31-1 Methyl (5S)-5-(Benzoyloxy)-7-bromohept-6-enoate 
• 76745-20-5 Methyl 5S-benzoyloxy-5-formylvalerate 
• 78606-81-2 Benzoic acid (2Z,5Z)-(S)-1-(3-methoxycarbonyl-propyl)-6-[(2R,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-hexa-2,5-dienyl ester 
• 71160-24-2 Leukotriene B 

Relevant academic research and scientific papers

12-Oxo-LTB4, a key pivotal intermediate in LTB4 metabolism

The first total synthesis of the very unstable and elusive biochemical intermediate 5(S)-hydroxy-12-oxo-6(Z),8(E),10(E),14(Z)-eicosatetraenoic acid (12-oxo-LTB4) (2) has been accomplished. Incubation of the synthetic 12-oxo-LTB4 (2) with human keratinocytes produced 5(S),12-dihydroxy-6-glutathionyl-7(E),9(E),14(Z)-eicosatrienoic acid (c-LTB3) and 5(S),12-dihydroxy-6-cysteinylglycyl-7(E),9(E),14(Z)-eicosatrienoic acid (d-LTB3), two new intriguing mediators which have been identified recently during the incubations of LTB4 with keratinocytes. We have also confirmed the identity of 12-oxo-LTB4 prepared from porcine leukocytes by comparison with the synthetic material and identified the formation in these incubates of the 6-trans-isomer of 12-oxo-LTB4.

A PRACTICAL METHOD FOR THE PRODUCTION OF METHYL 5(S)-BENZOYLOXY-5-FORMYLPENTANOATE - A KEY INTERMEDIATE IN THE SYNTHESIS OF LEUKOTRIENE B4

Catalytic epoxidation of methyl 7-hydroxy-5(E)-heptenoate by the Sharpless method gave optically pure (5R,6R)-methyl 5,6-epoxy-7-hydroxyheptanoate, in which regioselective opening of the epoxide ring by benzoic acid with the assistance of titanium tetrais

OPTICALLY ACTIVE PROPARGYLIC ALCOHOLS FROM D-XYLOSE USEFUL PRECURSORS FOR LTB4 SYNTHESIS

Using D-Xylose as a source of chirality at C-5 and C-12 in LTB4, an efficient synthesis of the optically active propargylic alcohols A and B, chiral precursors for the LTB4 synthesis, has been achieved.

A STEREOCONTROLLED AND EFFECTIVE SYNTHESIS OF LEUKOTRIENE B (1).

An efficient synthesis of leukotriene B (1) is reported which renders this important substance accessible in quantity.The process is convergent and includes a novel method for stereospecific generation of the conjugated triene unit.