252192-75-9

Upstream product

• 105850-89-3 chloromethyl (trimethylsilyl)methyl sulfide 
• 252192-73-7 N-((E)-3-benzyloxypropenoyl)-(1S)-camphorsultam 
• 154581-21-2 (E)-3-benzyloxypropenoyl chloride 
• 94594-90-8 (2R)-bornane-10,2-sultam 

Downstream Products

• 945927-22-0 C₂₁H₂₆OSSi 
• 945927-17-3 C₂₅H₂₉FN₂O₃SSi 
• 945927-16-2 C₂₅H₃₀N₂O₃SSi 
• 945927-14-0 C₂₆H₃₂N₂O₃SSi 
• 945927-13-9 C₂₈H₃₄O₄S₂Si 
• 945927-12-8 C₂₁H₂₈O₂SSi 
• 945927-11-7 C₂₈H₃₄O₂SSi 
• 112996-11-9 (2S,3R)-(-)-3-benzyloxy-2-methylbutan-1-ol 

Relevant academic research and scientific papers

Synthesis of butenolides recently isolated from marine microorganisms

The syntheses and 13C NMR analyses of four diastereomeric butenolides, two of which were recently isolated from the marine microorganisms Streptomycete B 5632 and Streptoverticillium luteoverticillatum 11014 are described. The two isolated butenolides were found to be one of the two diastereomers (4S,10R*,11R*)-4,11-dihydroxy-10-methyl-dodec-2-en-1,4-olide (RRS-1 or SSS-1) and one of the two diastereomers (4S,10S*,11R*)-4,11-dihydroxy-10-methyl-dodec-2-en-1,4-olide (SRS-1 or RSS-1). An asymmetric 1,3-dipolar cycloaddition of a thiocarbonyl ylide with a dipolarophile attached to camphorsultam and a ring-opening of an enantiomerically pure vinyloxirane by lithiated dithiane served as key steps for the construction of the three stereogenic centres. Further elaborations including ring-closing metathesis and Mitsunobu inversion furnished the four diastereomeric butenolides.

Synthesis of 4′-thionucleosides by 1,3-dipolar cycloadditions of the simplest thiocarbonyl ylide with alkenes bearing electron-withdrawing groups

Reactions of the simplest thiocarbonyl ylide with a variety of appropriate alkenes bearing electron-withdrawing substituents afforded the corresponding tetrahydrothiophenes, which could be easily elaborated into hydroxy and hydroxymethyl derivatives and t

Enantiomerically pure trans-3,4-disubstituted tetrahydrothiophenes from diastereoselective thiocarbonyl ylide addition to chiral α,β-unsaturated amides

(matrix presented). Asymmetric 1,3-dipolar cycloadditions of a sulfur-containing 1,3-dipole and α,β-unsaturated camphorsultam amides as dipolarophiles are described. The cycloaddition products, trans-3,4-disubstituted tetrahydrothiophenes, were obtained in high diastereomeric ratios (up to 90:10) and in high yields. Chromatographic removal of the minor diastereomer followed by cleavage of the chiral auxiliary furnished either the enantiomerically pure corresponding alcohol or carboxylic acid.