1233488-82-8

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 1233488-80-6 ethyl 2-O-benzyl-3,4,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 862537-76-6 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-β-D-glucopyranosyl)-benzoxazole 
• 1258410-90-0 3,4,6-tri-O-benzoyl-2-O-benzyl-β-D-glucopyranosyl thiocyanate 
• 72946-46-4 3,4,6-tri-O-benzoyl-2-O-benzyl-α-D-glucopyranosyl bromide 
• 100-39-0 benzyl bromide 
• 173987-57-0 ethyl 2-O-benzyl-1-thio-β-D-glucopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 1309361-03-2 ethyl 2-O-benzyl-3,4,6-tri-O-benzoyl-1-thio-α-D-glucopyranoside 
• 1610840-35-1 C₄₀H₃₄O₈S 
• 174172-99-7 ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

Hydrogen-bond-mediated aglycone delivery (HAD): A highly stereoselective synthesis of 1,2-cis α- D -glucosides from common glycosyl donors in the presence of bromine

Described herein is the expansion of the picoloyl protecting-group assisted H-bond mediated aglycone delivery (HAD) method recently introduced by our laboratory. At first it was noticed that high α-stereoselectivity is only obtained with S-ethyl glycosyl donors and only in the presence of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST), in high dilution, and low temperature. Combining the mechanistic studies of the HAD reaction and bromine-promoted glycosylations allowed a very effective method to be devised that allows for highly stereoselective α-glycosidation of practically all common leaving groups (S-phenyl, S-tolyl, S/O-imidates) at regular concentrations and ambient temperature.

Thioperoxide-mediated activation of thioglycoside donors

Thioperoxide (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a powerful thiophilic promoter system, capable of activating different thioglycosides. Both armed and disarmed thioglycosides were activated effectively in the

Glycosidation of thioglycosides in the presence of bromine: Mechanism, reactivity, and stereoselectivity

Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that β-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, α-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into α-bromide that is totally unreactive under the established reaction conditions.

Direct synthesis of diastereomerically pure glycosyl sulfonium salts

It is reported that stable glycosyl sulfonium salts can be generated via direct anomeric S-methylation of ethylthioglycosides. Mechanistically, this pathway represents the first step in the activation of thioglycosides for glycosidation; however, it can f

Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation

It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation expe

Comparison of the armed/disarmed building blocks of the D -gluco and d -glucosamino series in the context of chemoselective oligosaccharide synthesis

A very elegant Fraser-Reid armed-disarmed approach recently expanded to the building blocks of the superarmed and superdisarmed series shows very high utility in chemoselective oligosaccharide synthesis. Although a number of studies dedicated to the chemo