This pioneering work, which comprises the first literature example of the implementation of olefin metathesis in carbohydrate chemistry, formed the basis for later exploits by roy, for instance, the transformation of alkenyl lactosides into the corresponding symmetric pseudo-oligosaccharides.
Olefin metathesis: the nobel prize in chemistry of 2015 was shared by yves chauvin, robert hgrubbs and richard rschrock for their contributions to the field of olefin metathesis olefin metathesis  involves two olefin substrates which form a four-membered ring intermediate (first proposed by chauvin) and then rearrange the substituents to form two new carbon-carbon double bonds.
Request article pdf | olefin metathesis in carbohydrate chemistry | this account is devoted to a discussion of synthetic applications of olefin metathesis in carbohydrate chemistryolefin metathesis has emerged as a highly promising and exciting area in the contemporary organic synthesis of carbon-carbon bonds. Olefin metathesis has become an increasingly important and powerful tool in organic chemistry 1 ivin, k j and mol, j c 1997 olefin metathesis and olefin metathesis polymerization , 1st ed london : academic press. The former is converted into ribofuranoside 28, which is coupled with bromide 7 in the presence of zinc, and this is followed by ring-closing olefin metathesis subsequent overman rearrangement, dihydroxylation, and deprotection then affords the natural product. Olefin metathesis reaction type carbon-carbon bond forming reaction identifiers organic chemistry portal rsc ontology id.
Olefin metathesis in carbohydrate chemistry curr org journal of carbohydrate chemistry published online: 16 aug 2006 in memoriam jacques van boom (1937–2004) journal of carbohydrate chemistry published online: 16 aug 2006 browse journals by subject back to top area studies. Ruthenium-based olefin metathesis catalysts bearing carbohydrate-containing n-heterocyclic carbenes were synthesized and their structural characteristics analyzed.
Ruthenium-based olefin metathesis catalysts bearing carbohydrate-containing n-heterocyclic carbenes were synthesized and their structural characteristics analyzed the catalysts showed good to excellent activity in a variety of metathesis reactions, including ring-closing metathesis, ring-opening metathesis polymerization, cross-metathesis, and asymmetric ring-opening cross-metathesis. New crosslinked microcrystalline cellulose plastic films were made by olefin metathesis cellulose was first acylated under microwave irradiation by 10‐undecenoyl chloride in lithium chloride/n,n‐dimethylacetamide homogeneous solution to yield unsaturated fatty acid cellulose esters with a degree of substitution (ds) varying from 1 to 2. The metathesis-mediated transformation of carbohydrates into natural products and carbohydrate mimics has been covered in several reviews 12, 13 and fall outside the scope of this report this paper aims at giving an overview of the application of olefin metathesis in the synthesis of neoglycoconjugates.
Obviously, olefin metathesis in its various forms represents a particularly appealing chemical process for the design of small carbohydrate clusters (eg, dimers), glycomimetics, conformationally restrained oligosaccharides, and perhaps, more importantly, functionalized aglycones with pendant functionalities suitable for further neoglycoconjugate syntheses this chapter reports some of the applications in which the terminal alkene groups have been introduced in key positions around the ring. This account is devoted to a discussion of synthetic applications of olefin metathesis in carbohydrate chemistryolefin metathesis has emerged as a highly promising and exciting area in the.