13145-22-7

Upstream product

• 67-56-1 methanol 
• 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 
• 55881-04-4 methyl 2-O-methanesulfonyl-α-D-glucopyranoside 

Downstream Products

• 108866-70-2 BPh(Me-α-D-arabino-dHexp4,6H-2) 
• 87318-93-2 (2R,3S,4R,6S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol 
• 73541-94-3 methyl 2-deoxy-6-O-(triphenylmethyl)-α-D-arabinohexopyranoside 
• 74545-14-5 methyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranoside 
• 914924-81-5 ((2R,3S,4R,6S)-3-Benzyloxy-4,6-dimethoxy-tetrahydro-pyran-2-yl)-methanol 
• 902151-41-1 (2S,3S,4R,6S)-3-Benzyloxy-2-iodomethyl-4,6-dimethoxy-tetrahydro-pyran 
• 902151-39-7 (2R,3S,4R,6S)-3-Benzyloxy-4,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran 
• 53131-18-3 methyl O⁴,O⁶-(R)-benzylidene-O³-methyl-α-D-arabino-2-deoxy-hexopyranoside 
• 126257-19-0 Methyl 2-deoxy-3-O-methyl-6-O-triphenylmethyl-α-D-arabino-hexopyranoside 
• 135708-73-5 (5R,6S)-6-Benzyloxy-5-methoxy-cyclohex-2-enone 
• 902151-30-8 (2S,3R)-2-Benzyloxy-5-hydroxy-3-methoxy-cyclohexanone 
• 135708-69-9 (3S,4R,6S)-3-Benzyloxy-4,6-dimethoxy-2-methylene-tetrahydro-pyran 
• 87318-94-3 2-((2R,4S,6S)-4-Benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethanol 
• 87319-11-7 2-[(2R,4S,6S,8R,9S)-4-Benzyloxy-8-((S)-sec-butyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl]-ethanol 

Relevant academic research and scientific papers

Solvolyses of 2-Deoxy-α- and β-D-Glucopyranosyl 4′-Bromoisoquinolinium Tetrafluoroborates

The solvolyses of 2-deoxy-α- and β-D-glucopyranosyl 4′-bromoisoquinolinium tetrafluoroborates (1 and 2) were monitored in aqueous methanol, ethanol, trifluoroethanol, and binary mixtures of ethanol and trifluoroethanol. The observed rate constants are consistent with the solvolyses of 1 and 2 proceeding via dissociative (DN * AN) transition states. In comparison to the α-anomer, solvolysis of the β-compound gives a greater transition state charge delocalization onto the ring oxygen atom. Analysis of the solvolysis product ratios indicates that the 2-deoxyglucosyl oxacarbenium ion is not solvent-equilibrated in the solvent mixtures studied. In the solvolysis of compound 1, the solvent trifluoroethanol facilitates diffusional separation of the leaving group and, in so doing, promotes the formation of the retained trifluoroethyl glycoside.

Lithium aluminium hydride reduction of glycopyranoside-monosulfonates: Formation of branched furanosides

Lithium aluminum hydride reduction of glycopyranoside-monotosylates caused three reactions: (1) stereospecific 1,2-shift, producing branched furanosides (path A), (2) reductive O-S bond cleavage, producing the original glycosides (path B), and (3) reductive removal of the tosyloxy group, producing deoxyglycosides (path C). The path A reaction was particularly evident for the monotosylates at 2-O, 3-O, and 4-O: for example, methyl 2-O-tosyl-α-D-xylopyranoside gave methyl 2-deoxy-2-C-(hydroxymethyl)-α-D-α-erythrofuranoside in 60% yield. This reaction opens a new and efficient route to branched glycofuranosides of natural and unnatural type. Stereo-electronic requirements of this reaction in relation to the balance of the other two reactions are discussed.