7739-21-1

Basic information

• Product Name: 2,7-anhydro-manno-2-heptulopyranose
• Synonyms: 2,7-anhydro-manno-2-heptulopyranose
• CAS NO: 7739-21-1
• Molecular Weight: 192.169
• Mol File: 7739-21-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,7-anhydro-manno-2-heptulopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-anhydro-manno-2-heptulopyranose(7739-21-1)
• EPA Substance Registry System: 2,7-anhydro-manno-2-heptulopyranose(7739-21-1)

Safety Data

• Hazardous Substances Data: 7739-21-1(Hazardous Substances Data)

Upstream product

• 14694-95-2 Wilkinson's catalyst 
• 470-46-2 D-manno-2-heptulose 
• 108942-61-6 phenyl-α-D-manno-[2]heptulopyranoside 
• 3615-44-9 D-mannoheptulose 

Downstream Products

• 120857-21-8 Tetra-O-benzoyl-β-D-manno-2,7-anhydro-[2]heptulopyranose 
• 121292-31-7 tetrakis-O-(toluene-4-sulfonyl)-β-D-manno-2,7-anhydro-[2]heptulopyranose 

Relevant articles and documents

Metal-mediated decarbonylation and dehydration of ketose sugars

Ketose sugars can be decarbonylated and/or dehydrated by the action of certain metal complexes. Fructose reacts with 1 equiv of RhCl(PPh3)3 (1) in N-methyl-2-pyrrolidinone (NMP) at 130°C to give furfuryl alcohol, Rh(CO)Cl(PPh3)2 (2), and a small amount of 1-deoxyerythritol. 1,3-Dihydroxyacetone consumes 2 equiv of 1, giving methane and ca. 2 mol of 2. With manno-2-heptulose the primary product is 2,7-anhydromanno-2-heptulopyranose. The mechanisms of these unusual reactions have been studied by using 13C-labeling experiments and model reactions employing Pd(II) and HCl. Attempts to make the reactions catalytic using [Rh(Ph2PCH2CH2CH2PPh 2)2]+[BF4]- in place of 1 were not successful. The use of NMP as a solvent offers some advantages in the acid-catalyzed synthesis of certain carbohydrate dehydration products, as exemplified by the conversion of manno-2-heptulose to its 2,7-anhydride and of 2-deoxyglucose to 1-(2-furanyl)-1,2-ethanediol.