74590-47-9

Upstream product

• 74590-46-8 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 100-53-8 phenylmethanethiol 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 57030-42-9 2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide 
• 13242-53-0 acetobromomannose 
• 83-87-4 D-Mannose pentaacetate 

Downstream Products

• 437757-96-5 benzyl S,S-dioxo-2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 437757-83-0 benzyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

α-d-Mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II

Human Golgi α-mannosidase II (hGM) is a pharmaceutical target for the design of inhibitors with anti-tumor activity. Nanomolar inhibitors of hGM exhibit unwanted co-inhibition of the human lysosomal α-mannosidase (hLM). Hence, improving specificity of the

A new route to exo-glycals using the Ramberg-Baecklund rearrangement

A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Baecklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

INSULIN-LIKE, AND INSULIN-ANTAGONISTIC, CARBOHYDRATE DERIVATIVES. THE SYNTHESIS OF ARYL AND ARALKYL D-MANNOPYRANOSIDES AND 1-THIO-D-MANNOPYRANOSIDES

A number of novel, aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides were synthesized for evaluation of insulin-like and insulin-antagonistic properties.The substituted-phenyl α-D-mannopyranosides were prepared by the general procedure of Helferich and Schmitz-Hillebrecht, the substituted-phenyl 1-thio-α-D-mannopyranosides by a method corresponding to the Michael synthesis of aromatic glycosides, and the aralkyl 1-thio-α-D-mannopyranosides by aralkylation of 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranose 15 and subsequent O-deacetylation.Compound (15) was obtained by basic cleavage of the amidino group in 2-S-(tetra)-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide, the product of the reaction of tetra-O-acetyl-α-D-mannosyl bromide with thiourea.Benzyl 1-thio-β-D-mannopyranoside, obtained by reaction of the sodium salt of 1-thio-β-D-mannopyranose with α-bromotoluene, and benzyl 1-thio-α-L-mannopyranoside were also synthesized, in order to asses the stereospecificity of the biological activites measured.