105592-33-4

Upstream product

• 105592-35-6 benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside 
• 108182-78-1 (2R,3R)-3-((3aR,4S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,3-dihydroxy-propionic acid methyl ester 
• 105592-36-7 benzyl (E)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside 
• 108182-77-0 methyl uronate 
• 102919-04-0 benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 
• 108182-76-9 benzyl (E)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enodialdo-1,4-furanoside 
• 74912-02-0 1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose 
• 105592-37-8 5,6-anhydro-1-O-benzyl-2,3-O-isopropylidene-D-glycero-α-D-mannoheptofuranose 

Downstream Products

• 488-38-0 volemitol 
• 527-06-0 perseitol 

Relevant academic research and scientific papers

Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing

Abstract: A continuous flow procedure for the synthesis of methyl glycosides (Fischer glycosylation) of various monosaccharides using a heterogenous catalyst has been developed. In-depth analysis of the isomeric composition was undertaken and high consistency with corresponding results observed under microwave heating was obtained. Even in cases where addition of water was needed to achieve homogeneity—a prerequisite for the flow experiments—no detrimental effect on the conversion was found. The scalability was demonstrated on a model case (mannose) and as part of the target-oriented synthesis of d-glycero-d-manno heptose, both performed on multigram scale.

ON THE STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATIONS OF ALLYLIC SYSTEMS USED IN THE SYNTHESIS OF HIGHER-CARBON SUGARS

The stereochemistry of the major osmylation products of carbohydrate-based allylic alcohols can usually be predicted by application of Kishi's empirical rule.In particular, the addition of OsO4 can be formulated as taking place in the more abundant conformation on the surface anti to a pyranose or furanose ring-oxygen atom located at a stereocentre adjacent to the olefinic linkage.Exceptions to Kishi's empirical rule for osmylation are sometimes encountered with conjugated carbonyl compounds.

THE SYNTHESIS OF SOME SEVEN-CARBON SUGARS via THE OSMYLATION OF OLEFINIC SUGARS

The stereochemical outcome of the catalytic osmylation of 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-hept-6-enopyranose (10), 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose, (E)- and (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranose (20 and 27, respectively), methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate (26), (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hept-5-enofuranose, benzyl (E)- and (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside (46 and 50, respectively), and methyluronate (49) has been examined.Such oxidations led to satisfactory syntheses of L-glycero-D-gluco-heptose and the corresponding heptitol (from 20), L-glycero-D-gulo-heptitol (from 26), D-glycero-D-gluco-heptitol (from 27), D-glycero-D-galacto-heptitol (from 10 and 46), (meso)-glycero-gulo-heptitol (from 49), and D-glycero-D-manno-heptitol (from 50).