319475-24-6

Basic information

• Product Name: (3S,4R)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1R)-camphorsultam amide
• Synonyms: (3S,4R)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1R)-camphorsultam amide
• CAS NO: 319475-24-6
• Molecular Weight: 435.609
• Mol File: 319475-24-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,4R)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1R)-camphorsultam amide(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1R)-camphorsultam amide(319475-24-6)
• EPA Substance Registry System: (3S,4R)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1R)-camphorsultam amide(319475-24-6)

Safety Data

• Hazardous Substances Data: 319475-24-6(Hazardous Substances Data)

Upstream product

• 105850-89-3 chloromethyl (trimethylsilyl)methyl sulfide 
• 320385-10-2 (E)-3-benzyloxypropenoyl-(2'S)-bornane-10,2-sultam 

Downstream Products

• 319475-34-8 2-[(3R,4R)-(4-Benzyloxy-3-tetrahydrothienyl)methyl]-2-[(2'S,4'S)-2',4'-dimethyl-1'-octyl]-1,3-dithiane 
• 319475-28-0 (3R,4R)-3-(benzyloxy)-4-(bromomethyl)-tetrahydrothiophene 
• 319475-26-8 [(3R,4R)-4-(benzyloxy)-tetrahydrothiophene-3-yl]methanol 

Relevant articles and documents

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.