64694-22-0

Upstream product

• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 166733-02-4 S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N,N,N',N'-tetramethyl-N''-phenylphosphorodiamidimidothioate 
• 70893-32-2 2-benzothiazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 113533-73-6 (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran 
• 126709-14-6 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 216859-55-1 ethyl 2,3,4,6-tetra-O-benzyl-S-(N-tosylimino)-1-thio-β-D-glucopyranoside 
• 920749-29-7 Pent-4-enoic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 947335-87-7 O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) dichloro-cyanoacetimidate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 329365-86-8 ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide 
• 516-12-1 N-iodo-succinimide 

Relevant academic research and scientific papers

A 1,2-trans-Selective Glycosyl Donor Bearing Cyclic Protection at the C-2 and C-3 Hydroxy Groups

A new 1,2-trans-selective glycosylation reaction is described. Glucosyl donors protected cyclically at the C-2 and C-3 hydroxy groups as six- (butane diacetal), seven- (tetraisopropyldisiloxanylidene), or eight- (2,3-o-xylylene) membered fused rings were synthesized in a straightforward manner. The glycosylation reactions of the glucosyl donors with various acceptors mainly generated β-glycosides under conventional reaction conditions. The results show that the o-xylylene group is a suitable 1,2-trans-directing group from the points of view of stereoselectivity and chemical stability. A conformational study of the oxocarbenium ion of an o-xylylene-protected glucose derivative by NMR spectroscopy and computational simulation was carried out. The results imply that the oxocarbenium ion mainly adopts a 4H3 conformation owing to the rigid trans-fused ring at C-2 and C-3, while a noncyclically protected derivative might fluctuate between conformations. These results suggest that an eclipsing interaction between the pseudoequatorial xyloxy group at C-2 and the incoming nucleophile hampers 1,2-cis attack.

How the arming participating moieties can broaden the scope of chemoselective oligosaccharide synthesis by allowing the inverse armed-disarmed approach

(Chemical Equation Presented) A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety,

Dichloro-cyanoacetimidates as glycosyl donors

Transformation of 1-O-unprotected glucose and galactose derivatives (1a-d) into O-glycosyl dichloro-cyanoacetimidates (2a-d) was performed with dichloro-cyanoacetonitrile in the presence of DBU as base. Reaction with different acceptors (3a-d) under TMSOT

A new efficient glycosylation method employing glycosyl pentenoates and PhSeOTf

The PhSeOTf promoted glycosylations of various glycosyl acceptors with mannosyl pentenoates and glucosyl pentenoates as glycosyl donors afforded corresponding disaccharides in high yields. And the present glycosyl pentenoates/PhSeOTf method showed that th

Glycosyl disulfides: Novel glycosylating reagents with flexible aglycon alteration

Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning strategies.

Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groups

Glycosyl donors having a diphenylphosphinate and a propane-1,3-diyl phosphate leaving group were easily prepared by the addition of the anomeric hydroxyl group of 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranose to diphenylphosphinic and propane-1,3- diyldioxyphosphoryl chlorides. These glycosyl donors were selectively glycosylated with a number of primary and secondary oxygen nucleophiles in the presence of trimethylsilyl triflate (TMSOTf). The use of 1,3-diyl phosphate resulted in the stereoselective formation of β-O-linked glycosides.

An extremely mild and stereocontrolled construction of 1,2-cis-α-glycosidic linkages via benzyl-protected glycopyranosyl diethyl phosphites

A highly stereocontrolled 1,2-cis-α-glycosidation reaction under conditions mild enough for acid-labile alcohols has been developed using benzyl-protected glycopyranosyl diethyl phosphites as glycosyl donors in the presence of 2,6-di-tert-butylpyridinium

First synthesis of anomeric sulfimides - Efficient glycosyl donors

Sugar-derived anomeric sulfimides were prepared in high yields from the corresponding thioglycosides and their ability to act as glycosyl donors was investigated.

Preparation of glycosyl dimethylthiophosphates and their application as glycosyl donors

Benzyl- and acetyl-protected glycosyl dimethylthiophosphates were readily prepared from corresponding 1-hydroxyl sugars in good yield, and acted as very stable and efficient glycosyl donors in the construction of glycosidic bonds in the presence of variou

Solvent and Other Effects on the Stereoselectivity of Thioglycoside Glycosidations

Iodonium-ion mediated glycosidation of thioglycosides in toluene/1,4-dioxane gives much higher α-selectivities than the use of conventional glycosylation solvents. Furthermore, it is shown that the iodonium-ion source, concentration and presence of molecu