217814-68-1

Upstream product

• 108-98-5 thiophenol 
• 183388-13-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthaloylamino-α-D-glucopyranose 
• 174356-26-4 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3,4,5,6-tetra-chlorophthalimido)-D-glucospyranose 

Downstream Products

• 217814-90-9 thexyldimethylsilyl O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->4)-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 217814-87-4 thexyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-[(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 217814-79-4 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-[(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranosyl trichloroacetimidate 
• 217814-71-6 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-4-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 217814-86-3 C₄₃H₅₃Cl₄NO₁₆Si 
• 217814-74-9 Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-4-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester 
• 217814-89-6 C₄₆H₅₅Cl₄NO₁₃Si 
• 217814-88-5 C₄₆H₅₅Cl₄NO₁₃Si 
• 217814-73-8 Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-benzyloxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-hydroxy-6-phenylsulfanyl-5-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yloxy]-2-methyl-tetrahydro-pyran-4-yl ester 
• 217814-69-2 phenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 
• 286018-83-5 phenyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 
• 404391-07-7 phenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-(3,4,5,6-tetrachlorophthalimido)-β-D-thioglucopyranoside 
• 404391-02-2 4,5,6,7-Tetrachloro-2-((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 

Relevant academic research and scientific papers

Thioglycosylation of 1,2-cis-glycosyl acetates: A long-standing overlooked issue in preparative carbohydrate chemistry

1,2-cis-Glycosyl acetates with the α-configuration were revealed to be very unreactive towards Lewis acid catalyzed thioglycosylations. Optimal and cost-effective conditions for enabling this direct conversion is absent in the literature. Our studies have

Highly diastereoselective oxidation of 2-amino-2-deoxy-1-thio-β-D-glucopyranosides: Synthesis of imino sulfinylglycosides

A synthetic route to imino thioglycosides and to imino sulfinylglycosides has been developed. A detailed study on the diastereoselective oxidation of 2-amino-2-deoxy-1-thio-β-D-glucopyranosides is reported. It has been shown that the stereochemical outcome of the oxidation is highly dependent on the protective group of the amine function. While the oxidation of iminothioglycosides is slightly diastereoselective (up to 30% de in favor of the RS sulfoxide), a single isomer is obtained in the case of tetrachlorophthalimido derivatives. The absolute configuration of the sulfinyl glycoside was ascertained by NMR analysis using our recent model on the basis of the exo-anomeric effect corroborated by X-ray crystallography.

Synthesis of N-acetylglucosamine containing Lewis A and Lewis X building blocks based on N-tetrachlorophthaloyl protection - synthesis of Lewis X pentasaccharide

Phenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (5a) and thexyldimethylsilyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (5b) gave with O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)trichloroacetimidate (8) in the presence of BF3*Et2O as catalyst exclusively lactosamine derivatives 7a and 7b, respectively, in high yields.Ensuing reaction with O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate (9) in the presence of TMSOTf as catalyst afforded LeX trisacharide intermediates 10a,b.With fucosyl donor 9 and 5a,b as acceptors in the presence of TMSOTf as catalyst glycosylation either at the 3-O or the 4-O was observed, thus leading to mixtures of disaccharides 11a/12a and 11b/12b, respectively; their reaction with 8 furnished LeX trisaccharide intermediates 10a,b and Lea trisaccharide intermediates 14a,b.Transformation of 10b into the corresponding trichlotoacetimidate 17 and reaction with lactose acceptor 19 in the presence of Zn(OTf)2 as catalyst gave protected LeX pentasaccharide intermediate 21, which on deprotection led to unprotected LeX pentasaccharide 1. - Keywords: Glycosylation; Trichloroacetimidates; Protection; N-tetrachlorophthaloyl; Disaccharide, Trisaccharide building blocks; Lewis X; Lewis A