99679-79-5

Upstream product

• 98-88-4 benzoyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 26991-74-2 Methyl-4,6-O-benzyliden-2-O-benzoyl-3-deoxy-α-D-ribo-hexosid 
• 32469-91-3 methyl 2-O-benzoyl-4,6-O-benzylidene-3-deoxy-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

Modular hydroxyamide and thioamide pyranoside-based ligand library from the sugar pool: New class of ligands for asymmetric transfer hydrogenation of ketones

A large library of pyranoside-based hydroxyamide and thioamide ligands has been synthesized for asymmetric transfer hydrogenation in an attempt to expand the scope of the substrates to cover a broader range of challenging heteroaromatic and aryl/fluoroalkyl ketones. These ligands have the advantage that they are prepared from commercial D-glucose, D-glucosamine and α-amino acids, inexpensive natural chiral feedstocks. By carefully selecting the ligand components (substituents/configurations at the amide/thioamide moiety, the position of amide/thioamide group and the configuration at C-2), we found that pyranoside-based thioamide ligands provided excellent enantioselectivities (in the best cases, ees of >99% were achieved) in a broad range of ketones, including the less studied heteroaromatics and challenging aryl/fluoroalkyls. Note that both enantiomers of the reduction products can be obtained with excellent enantioselectivities by simply changing the absolute configuration of the thioamide substituent.

Enolates of Carbohydrates, 4. - Axial C-Alkylation in α-Position of α-Amino-α-deoxy-ketoses

Products of type 2a-c, 6, 10a, b, and 14a, b which are alkylated in α-position of the keto function are yielded by reaction of the α-amino-α-deoxy-uloses 1a-c, 5, 9a, and 13a, b with LDA, CH3I, HMPA in THF (method A) or KOtBu, CH3I in DMF (method B) in a