40789-24-0

Upstream product

• 27954-10-5 (S)-1-((3aR,4S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 5328-37-0 L-arabinose 
• 27954-10-5 Methyl 2,3-O-isopropylidene-α-L-gulofuranoside 
• 3458-28-4 D-Mannose 
• 84857-02-3 Methyl 6-O-benzoyl-2,3-O-isopropylidene-α-L-gulofuranoside 
• 1187858-68-9 Methyl 2,3-O-isopropylidene-α-D-gulofuranoside 
• 50692-25-6 Methyl 2,3-O-isopropylidene-5,6-di-O-methanesulfonyl-α-L-mannofuranoside 
• 26255-72-1 (3aR,4S,6aR)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 
• 7757-38-2 2,3;5,6-di-O-isopropylidene-D-gulonic acid γ-lactol 
• 70831-51-5 (R)-1-((3aS,4R,6aS)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 
• 55520-71-3 Methyl 5,6-di-O-benzoyl-2,3-O-isopropylidene-α-L-gulofuranoside 
• 74892-69-6 Methyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside 
• 50692-25-6 5,6-Di-O-methanesulfonyl-2,3-O-isopropylidene-α-D-mannofuranoside 

Downstream Products

• 161365-10-2 methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-mannofuranoside 
• 120202-54-2 6-azido-6-deoxy-D-mannopyranose 
• 138332-00-0 6-azido-6-deoxy-β-D-mannopyranose 
• 69434-52-2 Methyl 5-O-benzoyl-2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-L-mannofuranoside 
• 69434-52-2 Methyl 5-O-benzoyl-2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-gulofuranoside 
• 69434-52-2 Benzoic acid (S)-1-((3aS,4R,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-(toluene-4-sulfonyloxy)-ethyl ester 
• 497234-43-2 methyl (5R)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside 
• 497234-44-3 methyl (5S)-6-O-benzyl-5-(dimethoxyphosphinyl)-2,3-O-isopropylidene-α-D-lyxo-hexofuranoside 
• 497234-45-4 methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside 
• 497234-46-5 methyl (5S)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-β-L-gulofuranoside 
• 497234-42-1 methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose 
• 40823-53-8 methyl 2,3-O-isopropylidene-6-O-tosyl-α-D-lyxo-hexofuranos-5-ulose 

Relevant academic research and scientific papers

A new route for preparation of 5-deoxy-5-(hydroxyphosphinyl)-D-mannopyranose and -L-gulopyranose derivatives

Starting from methyl 2,3-O-isopropylidene-α-D-mannofuranoside (5), methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose (12) was prepared in three steps. The addition reaction of dimethyl phosphonate to 12, followed by deoxygenation of 5-

Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions

The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the

Inversion of regioselectivity in reactions of diols through the use of hexamethylenestannylene acetals as intermediates

Hexamethylenestannylene acetals obtained from a variety of carbohydrate-derived terminal 1,2-diols give good to excellent regioselectivity for tosylation at the secondary oxygen. In contrast, non-cyclic dialkylstannylene acetals react mainly at the primary oxygen. These results are attributed to the greater stability of the dominant stannylene acetal dimers for hexamethylenestannylene acetals.

SYNTHESIS OF EIGHT STEREOISOMERIC 5-(ADENIN-9-YL)-2,3,4-TRIHYDROXYPENTANOIC ACIDS

Condensation of 5-O-p-toluenesulfonyl-2,3-O-isopropylidene-D-ribonolactone (XIIIb) with sodium salt of adenine afforded compound XIV which on alkaline, followed by acid, hydrolysis gave the (2R,3R,4R)-isomer V.The (2S,3S,4S)-isomer VIII was prepared analogously from the L-ribonolactone derivative XVb via the adenine derivative XVI. Compound XVIIc was transformed by reaction with adenine into 6-(adenin-9-yl)-6-deoxy-D-glucose (XIX); similarly, 6-(adenin-9-yl)-6-deoxy-D-mannose (XXI) was prepared from the protected D-mannofuranoside XX.Oxidation of compounds XIX and XXI in alkaline medium afforded the (2S,3R,4R)-isomer VI, 1,2:3,4-Di-O-isopropylidene-D-galactopyranose (XXIIa) was transformed into 6-(adenin-9-yl)-6-deoxy-D-galactose (XXIIIb) which was oxidatively cleaved to give the (2S,3S,4R)-isomer VII.Methyl 5,6-di-O-methanesulfonyl-2,3-O-isopropylidene-D-mannofuranoside (XXVIb) was transformed into the reactive L-gulofuranoside derivative XXVIIe which on condensation with adenine and oxidative cleavage gave the (2S,3R,4S)-isomer IX.The (2R,3S,4R)-isomer XI was prepared analogously from the D-gulofuranose derivative XXXIb.Starting from L-mannose, the (2R,3S,3S)-derivative X was prepared via the 6-(adenin-9-yl)-6-deoxy-L-mannofuranoside derivative XXXc.Methyl 5-O-p-toluenesulfonyl-2,3-O-isopropylidene-L-lyxofuranoside XXXVb was transformed into 5-(adenin-9-yl)-5-deoxy-2,3-O-isopropylidene-L-lyxofuranose (XXXVII) which was oxidized to the lactone XXXVIII; this compound on successive alkaline and acid hydrolysis afforded the (2R,3R,4S)-isomer XII.