176037-22-2

Upstream product

• 176199-66-9 (R)-1-((8S,11R)-11-Methyl-7-oxa-1,5-dithia-spiro[5.5]undec-8-yl)-4-trimethylsilanyl-but-3-yn-2-ol 
• 62-23-7 4-nitro-benzoic acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 176037-02-8 4-(1,3-dithian-2-ylidene)pentanal 
• 1026936-22-0 (R)-4-Benzyl-3-((2R,3S)-2-bromo-6-[1,3]dithian-2-ylidene-3-hydroxy-heptanoyl)-oxazolidin-2-one 
• 176037-03-9 (8S,11R)-11-methyl-8-<(1R)-1-bromo-2-oxo-2-<(4R)-4-benzyl-2-oxo-1,3-oxazolidin-1,3-yl>ethyl>-7-oxa-1,5-dithiaspiro<5.5>undecane 
• 176037-05-1 (8S,11R)-8-(isopropoxycarbonylmethyl)-11-methyl-7-oxa-1,5-dithiaspiro<5.5>undecane 
• 176037-01-7 ethyl 4-(1,3-dithian-2-ylidene) pentanoate 
• 176037-06-2 (8S,11R)-11-methyl-8-(2-oxoethyl)-7-oxa-1,5-dithiaspiro<5.5>undecane 

Relevant academic research and scientific papers

Synthetic approaches to Rapamycin: Synthesis of a C10-C26 fragment via a one-pot Julia olefination reaction

Keys steps in a synthesis of the C10-C26 fragment of the immunosuppressant Rapamycin include (a) the use of a metallated benzothiazolyl sulfone in a one-pot Julia olefination to create the C21-C22 alkene stereoselectively and (b) a diastereoselective acid-catalysed cyclisation of a hydroxyl function onto a ketenedithioacetal (1,4-asymmetric induction) in order to create the oxane ring and fix the stereochemistry at C11.