155049-46-0

Upstream product

• 100-39-0 benzyl bromide 
• 376358-11-1 methyl 2,3,4-tri-O-trimethylsilyl-5-methylene-α-D-lyxopyranoside 
• 958643-54-4 methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-mannopyranoside 
• 1313193-62-2 C₂₁H₂₄O₅ 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 74247-81-7 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside 
• 105-60-2 caprolactam 
• 1270918-45-0 methyl 6-deoxy-6-N-piperidine-2-one-α-D-galctopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 50692-55-2 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-mannopyranoside 
• 155049-45-9 methyl-2,3,4-tri-O-acetyl-6-deoxy-α-D-luxo-hex-5-enopyranoside 

Downstream Products

• 845532-28-7 methyl 2,3,4-tri-O-benzyl-β-L-gulopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 1233944-58-5 (3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-one 
• 155155-66-1 C₂₇H₂₆O₄ 
• 1313193-65-5 (4R,5R,6S)-4,5,6-tris(benzyloxy)-2-iodocyclohex-2-en-1-one 
• 1313193-66-6 (4R,5R,6S)-4,5,6-tris(benzyloxy)-2-methylcyclohex-2-enone 
• 127545-53-3 (4R,5R,6S)-4,5,6-trihydroxy-2-methyl-2-cyclohexen-1-one 
• 1152509-46-0 (3S,4R,5R)-3,4,5-tris(benzyloxy)-1-decylpiperidin-2-one 
• 1233965-58-6 (3R,5R)-3,4,5-tris(benzyloxy)-1-decylpiperidine 

Relevant academic research and scientific papers

Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals

A novel Ferrier-type carbocyclization is reported. It involves a carbohydrate-derived lactone acetal synthesized from methyl α-d-glucopyranoside, which upon treatment with excess vinylmagnesium bromide provides a highly substituted carbocyclic product as a single stereoisomer. The yield is greatly increased when N,N,N′,N′-tetramethylethylenediamine is added to the reaction mixture. Optimized reaction conditions have been applied to lactone acetals derived from other carbohydrates. Based on the obtained results, a possible reaction mechanism has been proposed. Furthermore, scalability of the reaction up to 15 g scale and derivatization of the carbocyclic product has been demonstrated, including the formation of a rare trans-bicyclo[4.3.0]nonene scaffold via a ring-closing metathesis. The structure of this and all carbocyclic products were confirmed by X-ray crystallographic analysis.

Chiron approach to the total synthesis of Amaryllidaceae alkaloid (+)-lycoricidine

A highly stereoselective total synthesis of Amaryllidaceae alkaloid starting from α-D-galactopyranoside has been described. The salient features of this total synthesis are Ferrier carbocyclization reaction for the synthesis of ring A and Suzuki Miyaura c

NOVEL MANNOPYRANOSIDE DERIVATIVES WITH ANTICANCER ACTIVITY

The present invention relates to mannopyranoside-derived compounds and to the use thereof as medicaments, in particular in the treatment of cancer diseases, and also to the method for preparing same and to pharmaceutical compositions comprising such compo

Syntheses of (-)-gabosine A, (+)-4-epi-gabosine A, (-)-gabosine E, and (+)-4-epi-gabosine e

(+)-4-epi-Gabosine A 1 and (-)-gabosine A 2 have been synthesized starting from methyl α,d-glucopyranoside and methyl α,d-mannopyranoside, respectively, by utilizing Pd(0) catalyzed Stille coupling as the key step. On the other hand, syntheses of (+)-4-ep

Synthesis of novel sugar-lactam conjugates using the Aube reaction

An efficient and convenient method for the synthesis of sugar-lactam conjugates is reported starting from readily available sugar azides using the Aube reaction. Cyclic azido alcohols are used in the Aube reaction for the first time in a carbohydrate setting. The resulting glycoconjugates could be further used to increase the chemical diversity on the sugar backbone, and may find potential applications as glycomimetics, peptidomimetics, in glycotargeting and in CNS drug delivery.

A study of the epoxidation of 6-deoxyhex-5-enopyranosides. 1,5-Dicarbonyl derivatives and novel synthetic routes to D-xylo-hexos-5-ulose and D-lyxo-hexos-5-ulose

The work described deals with the isolation and characterization of epoxides from 6-deoxyhex-5-enopyranosides and preliminary exploration of their synthetic potential. Prolonged epoxidation reaction times led to their hydrolysis in situ and gave novel protected D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls). Some reactions of the hexos-5-uloses were studied, and in some cases septanoside (seven-membered-ring saccharide) derivatives were isolated. Novel routes to D-xylohexos-5-ulose and D-lyxo-hexos-5-ulose, of interest as intermediates in the synthesis and biosynthesis of inositols and aza sugars, are also described. The structures of the epoxides and novel hexos-5-uloses were established by NMR and X-ray crystallographic methods.

Novel carbocyclic ring closure of hex-5-enopyranosides

Retention of configuration at the anomeric carbon atom is observed for a novel rearrangement of carbohydrates. The readily accessible vinyl acetal 1 undergoes a triisobutylaluminum-assisted, stereoselective transposition of an oxygen atom on the ring with