117370-99-7

Upstream product

• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 117371-06-9 benzyl 6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 100-51-6 benzyl alcohol 

Downstream Products

• 118493-89-3 phenylmethyl 6,7-dideoxy-8-O-ethyl-α-D-manno-non-7-enopyranosidurononitrile 
• 191546-20-0 benzyl α-D-rhamnopyranoside 
• 1284280-87-0 benzyl 4-azido-2-O-benzoyl-4-deoxy-α-D-rhamnopyranoside 
• 1284280-86-9 benzyl 4-azido-4-deoxy-α-D-rhamnopyranoside 
• 1284280-85-8 benzyl 3,4-anhydro-2-O-benzoyl-6-deoxy-α-D-talopyranoside 
• 1284280-84-7 benzyl 2-O-acetyl-3,4-anhydro-6-deoxy-α-D-talopyranoside 
• 1284280-83-6 benzyl 3,4-anhydro-6-deoxy-α-D-talopyranoside 
• 1284280-82-5 benzyl 4-O-triflate-α-D-rhamnopyranoside 
• 1284280-81-4 benzyl 2,3-O-isopropylidene-4-O-triflate-α-D-rhamnopyranoside 
• 68124-06-1 benzyl 2,3-O-isopropylidene-α-D-rhamnopyranoside 
• 20595-77-1 3-deoxy-D-manno-2-octulosonic acid 
• 117371-04-7 phenylmethyl 8-carbethoxy-7-hydroxy-6-deoxy-α-D-manno-octopyranoside 2,3,4-tri-O-acetate 
• 116406-15-6 phenylmethyl 6-deoxy-6-iodo-α-D-mannopyranoside 2,3,4-tri-O-acetate 

Relevant academic research and scientific papers

An efficient synthesis of selectively functionalized D-rhamnose derivatives

D-Rhamnose is an important component of bacterial lipopolysaccharides. This paper describes a short and highly efficient synthesis of D-rhamnose from D-mannose. The synthesis of selectively C-4 modified d-rhamnosides and 6-deoxy-D-talosides as potential building blocks for complex oligosaccharide synthesis is also discussed.

A Novel Strategy for the Synthesis of Ammonium 3-Deoxy-D-manno-2-octulosonate (Ammonium KDO) from Lower Monosaccharides. C-C Bond Construction at C6 of D-Mannose via Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling

Our synthesis of ammonium 3-deoxy-D-manno-2-octulosonate (ammonium KDO, 16) from D-mannose (3) proceeds in 10 one-flask operations in 1.5-1.6percent overall yield (66percent per operation).The strategic reaction is a C-C bond construction at C6 of D-mannose via photochemically induced radical cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose, in aqueous ethanol without protection of carbohydrate hydroxyls.In this paper we provide full experimental details of our KDO synthesis.In addition we provide some observations and insights on vanadium-catalyzed oxidations of α-hydroxy acids to α-keto acids.

A SYNTHESIS OF AMMONIUM 3-DEOXY-D-MANNO-2-OCTULOSONATE (AMMONIUM KDO) FROM D-MANNOSE VIA COBALOXIME-MEDIATED RADICAL ALKYL-ALKENYL CROSS COUPLING

We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-D-manno-2-octulosonic acid (KDO) starting from D-mannose.The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxim mediated radical alkyl-alkenyl cr

ALKYL-ALKENYL CROSS COUPLING VIA ALKYL COBALOXIME RADICAL CHEMISTRY. AN ALKYL EQUIVALENT TO THE HECK REACTION COMPATIBLE WITH COMMON ORGANIC FUNCTIONAL GROUPS

A novel cobalt-mediated radical-olefin coupling reaction is described which regenerates the olefin functionality in the final product.The regeneration of olefin functionality is unique among radical-olefin couplings using simple activated alkenes.