1192034-03-9

Basic information

• Product Name: (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one
• Synonyms: (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one
• CAS NO: 1192034-03-9
• Molecular Weight: 429.604
• Mol File: 1192034-03-9.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one(1192034-03-9)
• EPA Substance Registry System: (2R,3S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-5-(benzyloxy)-3-hydroxy-2-methylpentan-1-one(1192034-03-9)

Safety Data

• Hazardous Substances Data: 1192034-03-9(Hazardous Substances Data)

Upstream product

• 863324-53-2 (R)-1-(4-benzyl-2-thioxothiazolidin-3-yl)propan-1-one 
• 19790-60-4 3-Benzyloxypropanal 

Downstream Products

• 1192034-05-1 C₂₉H₄₁NO₃S₂Si 
• 503620-04-0 (2S,3S)-5-(benzyloxy)-2-methylpentane-1,3-diol 

Relevant articles and documents

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A highly stereoselective synthesis of the C-8-C-24 fragment of maltepolide C has been achieved in a convergent and efficient manner by utilizing a tandem Sharpless asymmetric dihydroxylation (SAD)/SN2 cyclization reaction sequence as the key st

Total synthesis and stereochemical assignment of (-)-ushikulide A

We report the determination of the full stereostructure of (-)-ushikulide A (1), a spiroketal containing macrolide by total synthesis. Ushikulide A (1) was isolated from a culture broth of Streptomyces sp. IUK-102 and exhibits potent immunosuppressant activity (IC50 = 70 nM). To embark upon an ushikulide A synthesis, a tentative assignment was made based on analogy to cytovaricin (2), a related macrolide isolated from a culture of Streptomyces diastatochromogenes whose full structure was previously established via synthesis and X-ray crystallography. This report delineates studies on several key steps, namely a direct aldol reaction catalyzed by the dinuclear zinc ProPhenol complex, a metal catalyzed spiroketalization, as well as application of an unprecedented asymmetric alkynylation of a simple saturated aldehyde with methyl propiolate to prepare the nucleophilic partner for a Marshall-Tamaru propargylation. These studies culminated in the first total synthesis and stereochemical assignment of (-)-ushikulide A and significantly extended the scope of the above-mentioned methodologies.