3971-45-7

Upstream product

• 67-56-1 methanol 
• 1949-89-9 2-deoxy-D-galactose 
• 21193-75-9 D-galactal 
• 36396-42-6 Methyl-3,4,6-tri-O-benzoyl-2-desoxy-α-D-lyxo-hexopyranosid 
• 7647-01-0 hydrogenchloride 
• 19877-02-2 methyl 4,6-O-benzylidene-2-deoxy-α-D-lyxo-hexopyranoside 
• 13265-84-4 D-glucal 
• 53685-07-7 Methyl 3,4-O-isopropylidene-6-O-triphenylmethyl-α-D-galactopyranoside 
• 23568-30-1 2-Deoxy-L-arabino-hexose 
• 20770-58-5 Acetic acid (1S,2S)-2,3-diacetoxy-1-((S)-1,2-diacetoxy-ethyl)-4-nitro-butyl ester 
• 87858-15-9 3,4,5,6-Tetra-O-acetyl-1,2-dideoxy-1-nitro-L-arabino-hexitol 
• 87858-14-8 3,4,5,6-Tetra-O-acetyl-1,2-dideoxy-1-nitro-L-arabino-hex-1-enitol 
• 40269-01-0 methyl 3,4-O-isopropylidene-α-D-galactopyranoside 
• 81562-22-3 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-4-O-mesyl-D-arabino-hex-1-enitol 

Downstream Products

• 128536-91-4 Methyl 3,6-di-O-benzoyl-2-deoxy-α-D-lyxo-hexopyranoside 
• 18981-64-1 Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 
• 85439-70-9 methyl-3,4-anhydro-2,6-didesoxy-α-L-lyxo-hexopyranoside 
• 19129-68-1 Methyl 3-azido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 4-benzoate 
• 18981-62-9 methyl 3-azido-2,3,6-trideoxy-4-O-methanesulphonyl-α-L-arabino-hexopyranoside 
• 67758-43-4 Methyl 2,6-dideoxy-α-L-arabino-hexopyranoside 3,4-di-p-toluenesulfonate 
• 18981-61-8 Methyl 2,6-dideoxy-α-L-arabino-hexopyranoside 3-p-toluenesulfonate 
• 54623-22-2 methyl-3-azido-2,3,6-tridesoxy-α-L-arabino-hexopyranoside 
• 19131-10-3 methyl-2,6-didesoxy-α-L-arabino-hexopyranoside 
• 67758-44-5 Methyl 2,6-dideoxy-α-L-arabino-hexopyranoside 4-p-toluenesulfonate 
• 54623-23-3 methyl-3-amino-2,3,6-tridesoxy-α-L-arabino-hexopyranoside 
• 18977-92-9 methyl α-L-daunosaminide 
• 87782-53-4 Methyl 2-deoxy-β-L-arabino-hexopyranoside 6-p-toluenesulfonate 
• 87782-52-3 Methyl 2-deoxy-α-L-arabino-hexopyranoside 6-p-toluenesulfonate 

Relevant academic research and scientific papers

A Unified Strategy to Access 2- And 4-Deoxygenated Sugars Enabled by Manganese-Promoted 1,2-Radical Migration

The selective manipulation of carbohydrate scaffolds is challenging due to the presence of multiple, nearly chemically indistinguishable O-H and C-H bonds. As a result, protecting-group-based synthetic strategies are typically necessary for carbohydrate modification. Here we report a concise semisynthetic strategy to access diverse 2- and 4-deoxygenated carbohydrates without relying on the exhaustive use of protecting groups to achieve site-selective reaction outcomes. Our approach leverages a Mn2+-promoted redox isomerization step, which proceeds via sugar radical intermediates accessed by neutral hydrogen atom abstraction under visible light-mediated photoredox conditions. The resulting deoxyketopyranosides feature chemically distinguishable functional groups and are readily transformed into diverse carbohydrate structures. To showcase the versatility of this method, we report expedient syntheses of the rare sugars l-ristosamine, l-olivose, l-mycarose, and l-digitoxose from commercial l-rhamnose. The findings presented here validate the potential for radical intermediates to facilitate the selective transformation of carbohydrates and showcase the step and efficiency advantages attendant to synthetic strategies that minimize a reliance upon protecting groups.

Synthesis and biological activities of methyl oligobiosaminide and some deoxy isomers thereof.

Methyl oligobiosaminide (1) the core structure of oligostatin C, and five analogues, the 6-hydroxy-(2), 2-deoxy- (3), 2-deoxy-6-hydroxy- (4), 3-deoxy- (5), and 3-deoxy-6-hydroxy derivatives (6), were synthesized by coupling the protected pseudo-sugar epoxide 46 with suitable methyl 4-amino-4-deoxy-alpha-D-hexopyranoside derivatives. Compounds 3 and 6 showed notable inhibitory activity against alpha-D-glucosidase and alpha-D-mannosidase, respectively, whereas compound 1 had almost no activity.

CATION-EXCHANGE RESIN-CATALYZED ADDITION OF METHANOL TO BENZOYLATED 1,5-ANHYDRO-2-DEOXY-D-HEX-1-ENITOLS

1,5-Anhydro-3,4,5-tri-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (1) was boiled under reflux with methanol and AG 50W-X8 cation-exchange resin.A two-product mixture of glycosides (2 and 3) was obtained in 38percent yield, together with 19percent of unreacted material. 1,5-Anhydro-3,6-di-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (7) was prepared from 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol by selective benzoylation, from wich the corresponding 4-methansulphonate 8 was obtained.Treatment of 8 with sodium benzoate in hexamethylphosphoric triamide for 72 h at 100 deg C afforded 1,5-anhydro-3,4,6-tri-O-benzoyl-2-deoxy-D-xylo-hex-1-enitol (9) in 52percent yield.An unknow byproduct (B), tentitatively shown to be a tri-O-benzoyl-D-hex-2-enopyranose analog, was also isolated in 14percent yield.The 270-MHz n.m.r. spectrum of B was analyzed in terms of its J1,3, J2,4 and J4,5 coupling constant in relation to the various configurational and conformational possibilities for hex-2-enopyranose, and was identified as 1,4,6-tri-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranose having the oH5 conformation.The analysis presented should also be applicable to pent-2-enopyranose systems.When 9 was treated with methanol in the presence of AG 50W-X8 cation-exchange resin, a mixture of glycosides 4 and 5 was obtained in 47percent yield.The low yields were attributed to methanolysis of the benzoyl groups during the reaction.

SYNTHESIS OF METHYL 2,6-DIDEOXY-α-D-XYLO- AND α-D-LYXO-HEXOPYRANOSIDE

Synthesis of the title glycosides from methyl 3,4-anhydro-6-deoxy-α-D-galactopyranoside and 2-deoxy-D-lyxo-hexopyranose is described.