168138-16-7

Upstream product

• 100-39-0 benzyl bromide 
• 126113-70-0 phenyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 168138-14-5 phenyl 3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside 
• 168138-26-9 phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-98-5 thiophenol 
• 83-87-4 D-Mannose pentaacetate 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 316188-12-2 phenyl 6-O-[(tert-butyl)diphenylsilyl]-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 310870-40-7 phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside 
• 316188-14-4 phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 126092-08-8 phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 196697-67-3 (2R,4aR,6R,7S,8S,8aR)-8-Allyloxy-7-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 512171-19-6 (2R,3R,4S,5S,6R)-4-Allyloxy-5-benzyloxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 

Downstream Products

• 316188-15-5 phenyl 2,4,6-tri-O-benzyl-3-O-(3-carboxypropanoyl)-1-thio-α-D-mannopyranoside 
• 512171-21-0 ((2R,3R,4S,5S,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-4-yloxy)-tert-butyl-diphenyl-silane 
• 168138-17-8 phenyl 2,4,6-tri-O-benzyl-3-O-carbamoyl-1-thio-α-D-mannopyranoside 
• 168138-19-0 2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl trichloroacetimidate 
• 168138-21-4 (1'R,2R,2'R,4R,5S)-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-5-hydroxy-2-phenyl-1,3-dioxane 
• 168138-20-3 (1'R,2R,2'R,4R,5S)-5-acetoxy-4-[1-benzyloxy-2-(2,4,6-tri-O-benzyl-3-O-carbamoyl-α-D-mannopyranosyl)oxy-3-butenyl]-2-phenyl-1,3-dioxane 
• 1599455-72-7 phenyl-4,6-O-benzylidene-2-O-benzoyl-3-O-methyl-α-D-mannopyranosyl-(1-6)-(2-O-benzoyl-4-O-benzyl-3-O-methyl-α-D-mannopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 1400562-20-0 phenyl 2,4,6-tri-O-benzyl-3-O-chloroacetyl-1-thio-α-D-mannopyranoside 
• 1400562-57-3 2,4,6-tri-O-benzyl-3-O-chloroacetyl-α-D-mannopyranosyl fluoride 
• 1400562-58-4 2,4,6-tri-O-benzyl-3-O-chloroacetyl-β-D-mannopyranosyl fluoride 
• 1393109-92-6 1-O-acetyl-3-O-benzoyl-2,4,6-tri-O-benzyl-β-D-mannopyranose 
• 1393109-78-8 1-O-acetyl-3-O-benzoyl-2,4,6-tri-O-benzyl-α-D-mannopyranose 
• 1393109-98-2 3-O-benzoyl-2,4,6-tri-O-benzyl-β-D-mannopyranose 
• 1393109-86-8 3-O-benzoyl-2,4,6-tri-O-benzyl-α-D-mannopyranose 

Relevant academic research and scientific papers

Desilylation under high pressure

Cleavage of tert-butyldiphenylsilyl (TBDPS) ether was examined under high pressure conditions (1.0 GPa) using HF/pyridine in DMF. This method proved to be exceptionally suitable for deprotecting the TBDPS group that resides at the sterically hindered posi

Chemical synthesis of asparagine-linked archaeal N-glycan from Methanothermus fervidus

Several N-linked glycoproteins have been identified in archaea and there is growing evidence that the N-glycan is involved in survival and functioning of archaea in extreme conditions. Chemical synthesis of the archaeal N-glycans represents a crucial step

Single-step multisyntheses of glycosyl acceptors: Benzylation of n-1 hydroxyl groups of phenylthio glycosides of xylose, mannose, glucose, galactose, 2-azido-2-deoxy-glucose, and 2-azido-2-deoxy-galactose

An array of synthons is required to access an oligosaccharide library; however, multistep and thus time-consuming synthesis is inevitable. To rapidly access such synthetic units, multiple benzylation reactions of monosaccharides under phase-transfer condi

Synthesis of monoglucosylated high-mannose-type dodecasaccharide, a putative ligand for molecular chaperone, calnexin, and calreticurin

Convergent and stereoselective synthetic routes to Man9GlcNAc2 (1b), α-Glc1M9GlcNAc2 (2b), and its stereoisomer β-Glc1M9GlcNAc2 (3) were established. Interaction analy

Prearranged glycosides. Part 12. Intramolecular mannosylations of glucose derivatives via prearranged glycosides

A series of prearranged glycosides 5, 17, 23, 28, 37, and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4, and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding tethered (1 → 4)-linked disaccharides. The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: Sugar moiety of antitumor antibiotic bleomycin

A new route to the disaccharide moiety (2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose) of the antitumor agent bleomycin was developed. Both the L-gulose synthon 21 and the 3-O-carbamoyl-D-mannose segment 30 were prepared from D-mannose in a regioselective manner by applying stannylene acetal methodology. Glycosylation of 21 with 30 proceeded smoothly, and further conversion to disaccharide derivatives (33 and 34) was successfully accomplished.

Preparation of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose: Synthetic study on the sugar moiety of antitumor antibiotic bleomycin

A new practical route to the disaccharide moiety of bleomycin was developed. Both of key building blocks 9 and 16 were prepared from D-mannose in a regioselective manner by applying stannylene acetal methodology. Glycosylation of the allyl alcohol 9 with the trichloroacetimidate 16 proceeded smoothly, and the further incorporation to the disaccharide moiety was succesfully accomplished.