20595-77-1

Basic information

• Product Name: 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID, AMMONIUM SALT
• Synonyms: KDO
• CAS NO: 20595-77-1
• Molecular Formula: C8H17NO8
• Molecular Weight: 255.22
• Mol File: 20595-77-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID, AMMONIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID, AMMONIUM SALT(20595-77-1)
• EPA Substance Registry System: 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID, AMMONIUM SALT(20595-77-1)

Safety Data

• Hazardous Substances Data: 20595-77-1(Hazardous Substances Data)

Upstream product

• 25218-26-2 (R)-3-Hydroxy-5-(1,2,3,4-tetrahydroxy-butyl)-dihydro-furan-2-one 
• 25218-26-2 (R)-3-Hydroxy-5-((1S,2R,3R)-1,2,3,4-tetrahydroxy-butyl)-dihydro-furan-2-one 
• 328-42-7 Oxalacetic acid 
• 5328-37-0 L-arabinose 
• 50-69-1 D-ribose 
• 1114-34-7 D-lyxose 
• 117371-04-7 phenylmethyl 8-carbethoxy-7-hydroxy-6-deoxy-α-D-manno-octopyranoside 2,3,4-tri-O-acetate 
• 118493-90-6 phenylmethyl 6,7-dideoxy-8-O-ethyl-α-D-manno-non-7-enopyranosidurononitrile 2,3,4-tri-O-acetate 
• 117371-05-8 8-carbethoxy-7-hydroxy-6-deoxy-α-D-manno-octopyranose 2,3,4-tri-O-acetate 
• 117371-06-9 benzyl 6-O-p-toluenesulfonyl-α-D-mannopyranoside 
• 116406-15-6 phenylmethyl 6-deoxy-6-iodo-α-D-mannopyranoside 2,3,4-tri-O-acetate 
• 118493-89-3 phenylmethyl 6,7-dideoxy-8-O-ethyl-α-D-manno-non-7-enopyranosidurononitrile 
• 117370-99-7 phenylmethyl 6-deoxy-6-iodo-α-D-mannopyranoside 
• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 

Relevant articles and documents

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.

Structural Analogs of 2-Keto-3-deoxy-D-mannooctulosonic Acid

The synthesis of 3-deoxy sugars (4-8) has been carried out as structural analogs of 2-keto-3-deoxy-D-mannooctulosonic acid (KDO; 1).