85398-14-7

Upstream product

• 50-00-0 formaldehyd 
• 89064-70-0 2,3,4,6-Tetra-O-benzyl-1-desoxy-1-nitro-D-glucopyranose 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 133191-78-3 3,4,5,7-tetra-O-benzyl-1-O-(methoxymethyl)-α,β-D-gluco-2-heptulopyranose 
• 133191-79-4 methyl 3,4,5,7-tetra-O-benzyl-α-D-gluco-2-heptulopyranoside 

Downstream Products

• 1357160-40-7 1-deoxy-1-chloro-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose 
• 1357160-39-4 1-O-tosyl-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose 
• 1357160-43-0 1-deoxy-1-(2-naphthalenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 1357160-42-9 1-deoxy-1-(p-methoxyphenylamino)-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose 
• 1357160-41-8 1-deoxy-1-amino-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose 
• 1357160-51-0 (5S,7R,8S,9S,10R)-8,9,10-trihydroxy-7-(hydroxymethyl)-N-(4-methoxyphenyl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane-2,2-dioxide 
• 1357160-49-6 (5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-(benzyloxymethyl)-N-(4-methoxyphenyl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane-2,2-dioxide 
• 1357160-47-4 (5S,7R,8R,9S,10R)-8,9,10-tri(benzyloxy)-7-(benzyloxymethyl)-1-(tert-butyloxy)-3-(4-methoxyphenyl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane-2,2-dioxide 
• 1357160-46-3 (5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-(benzyloxymethyl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane-2,2-dioxide 
• 1192412-18-2 (5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-1-tert-butoxycarbonyl-3,6-dioxa-2-thia-1-azaspiro[4.5]decane-2,2-dioxide 
• 1192412-19-3 (5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-1-methoxycarbonyl-3,6-dioxa-2-thia-1-aza-spiro[4.5]decane-2,2-dioxide 
• 133191-84-1 2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-7-O-(triphenylmethyl)-D-glycero-D-gulo-heptitol 
• 133191-81-8 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol 

Relevant academic research and scientific papers

Expedient and versatile formation of novel amino-deoxy-ketoheptuloses

Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-keto

Highly efficient synthesis of ketoheptoses

A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.

Regioselective synthesis and biological evaluation of spiro-sulfamidate glycosides from exo-glycals

We report the synthesis of spiro-sulfamidate glycosides from exo-glycals. This route is regioselective and furnishes an original class of spiro-hydantoin glycoside analogues. A biological evaluation of this family on a range of glycosidases shows that these compounds are weak but very selective inhibitors of α-glucosidase and amyloglucosidase.

A Ramberg-Baecklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Baecklund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Baecklund rearrangement is also reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides

Cycloglycosylation of 3,4,5,7-tetra-O-benzyl-α-D-hept-2-ulopyranoses (2a-c) was carried out stereoselectively under the catalysis of Lewis acid to afford two spiro-cyclodisaccharides 3a-c and 4a-c in good yields. The reaction provided the kinetic products 3a-c or the thermodynamic products 4a-c as the predominant products under different conditions, respectively. The unprotected disaccharides 5a-c and 6a-c and the acetylated derivatives 7a-c and 8a-c were prepared by catalytic hydrogenation and followed by acetylation. The structures of compounds 4a-c, 6a-c and 8a-c were confirmed to be α,β-anomeric configuration with chair-chair-chair form for the tri-cycles based on the X-ray crystallographic analysis of 6a-c. The α,α-anomeric configurations of compounds 3a-c, 5a-c and 7a-c were determined based on the measurements of the three bond coupling constants 3JC,H between the C-1 and the H-3 of 7a-c.

Synthetic applications of Ramberg-Backlund derived exo-glycals

Synthetic applications of the title glycals, prepared from S-glycoside dioxides using the Meyers' variant of the Ramberg-Backlund rearrangement are described. These include a formal total synthesis of a novel β-glycosidase inhibitor, and an efficient route to spirocyclic glucose derivatives. In addition, silyl methodology has been developed which allows unprotected exo- glycals to be synthesised.

Conversion of D-Glucose to L-Glucose: Oxidative Decarboxylation of α-Oxy Carboxylic Acids via Their Diacyl Peroxides

D-Glucose was converted to an L-glucose derivative.The key step was the oxidative decarboxylation of carboxylic acid 12 via its diacyl peroxide derivative.This synthetic scheme proceeds through C-glycosidic compounds and is applicable to other sugar confi

Desoxy-nitrozucker. Synthese von Ketosen durch Kettenverlaengerung von 1-Desoxy-1-nitroaldosen. Nucleophile Additionen und Solvolyse von Nitroaethern

A method for the preparation of chain elongated uloses based upon the base-catalyzed addition of 1-deoxy-1-nitroaldoses to aldehydes and Michael acceptors and subsequent solvolytic replacement of the nitro group by a hydroxy group is described.Thus, addit