5397-35-3

Upstream product

• 5349-37-1 (3R,4S,5R,6R)-1,3,4,5,6,7-Hexahydroxy-heptan-2-one 
• 3019-74-7 sedoheptulose 
• 100816-37-3 hexa-O-acetyl-keto-D-altro-[2]heptulose 
• 22224-54-0 D-idohept-2-ulose 
• 3615-44-9 D-mannoheptulose 
• 14694-95-2 Wilkinson's catalyst 
• 470-46-2 D-manno-2-heptulose 
• 22224-53-9 L-gulo-1,3,4,5,6,7-Hexahydroxy-heptan-2-on 
• 108942-61-6 phenyl-α-D-manno-[2]heptulopyranoside 
• 625-48-9 2-nitro-1-ethanol 
• 50-69-1 D-ribose 
• 2893-24-5 phenyl-α-D-gluco-[2]heptulopyranoside 
• 58-86-6 D-xylose 
• 75-52-5 nitromethane 

Relevant academic research and scientific papers

Facile and efficient synthesis of ido-heptulosan via a strategy derived from Mo(VI)-catalysed reactions

A simple and high-yielding method for the preparation of 2,7-anhydro-β-D-ido-heptulopyranose (IDO) is described. It utilises the ability of molybdate ions to create the conditions for the skeletal rearrangement in the molecule of 2-C-branched aldose. This evidence is used in the synthesis of IDO from 2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-D-gulofuranose in one step. The title compound is obtained in 95percent yield.

Synthesis of sedoheptulose from 2-C-(hydroxymethyl)-D-allose by molybdic acid-catalysed carbon-skeleton rearrangement

A new branched-chain aldose, 2-C-(hydroxymethyl)-D-allose (3), was obtained by a base-catalysed addition of 2,3:5,6-di-O-isopropylidene-β-D-allofuranose to formaldehyde followed by acid hydrolysis of the aldol product. On treatment with a catalytic amount of molybdic acid at 90°C, 3 afforded its equilibrium mixture with sedoheptulose tautomeric and anhydro forms in the ratio 12:1. Sedoheptulose in its 2,7-anhydro form, 2,7-anhydro-β-D-altro-heptulopyranose, was obtained from this mixture by treatment with 0.5 M H2SO4 and crystallisation (overall 63% yield). Copyright (C) 1999 Elsevier Science Ltd.

Hydroxymethylation of aldonolactones and a chemical synthesis of 3-deoxy-3-fluoro-D-fructose

(Benzyloxymethyl)lithium, generated in situ from butyllithium and (benzyloxymethyl)tri-n-butylstannane, was found to be an efficient reagent for the monohydroxymethylation of aldono 1,4-lactones to form ketoses.Thus, 4-hydroxy butanoic-1,4-lactone, 2-deoxy-2-fluoro-3,5-di-O-(methoxymethyl)-D-arabinono-1,4-lactone, 2,3,5-tri-O-(methoxymethyl)-D-arabinono-1,4-lactone, 5-O-(methoxymethyl)-2,3-O-methylidene-D-ribono-1,4-lactone, 2,3,5,6-tetra-O-(methoxymethyl)-D-altrono-1,4-lactone, 2,3:5,6-di-O-isopropylidene-D-gulono-1,4-lactone and 2,3-O-isopropylidene-L-erythrono-1,4-lactone were respectively converted to 1-benzyloxy-5-hydroxy-2-pentanone, 1-O-benzyl-3-deoxy-3-fluoro-4,6-di-O-(methoxymethyl)-D-fructofuranose, 1-O-benzyl-3,4,6-tri-O-(methoxymethyl)-D-fructofuranose, 1-O-benzyl-6-O-(methoxymethyl)-2,3-O-methylidene-D-psicofuranose, 1-O-benzyl-3,4,6,7-tetra-O-(methoxymethyl)-D-altro-heptulofuranose, 1-O-benzyl-3,4:6,7-di-O-isopropylidene-D-gulo-heptulofuranose, and 1-O-benzyl-3,4-O-isopropylidene-L-erythro-pentulofuranose in 63-81percent yields.By deprotection of 1-O-benzyl-3-deoxy-3-fluoro-4,6-di-O-(methoxymethyl)-D-fructose, 3-deoxy-3-fluoro-D-fructose was prepared for the first time.

An efficient synthesis of sedoheptulose catalyzed by spinach transketolase

A practical procedure for transketolase catalyzed condensation of hydropyruvic acid with D-ribose has been used for the synthesis of D-sedoheptulose.

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.

SEDOHEPTULOSE DIGALLATE FROM CORNUS OFFICINALIS

A chemical investigation of the leaves of Cornus officinalis has led to the isolation and characterization of a novel gallotannin, 1,7-di-O-galloyl-D-sedoheptulose, in addition to six galloylglucoses and five ellagitannins.The structure of the new compound was established on the basis of spectroscopic and chemical evidence.This is the first gallotannin possessing a heptose core.Key Word Index - Cornus officinalis; Cornaceae; 1,7-di-O-galloyl-D-sedoheptulose; D-sedoheptulose; gallotannin; tannin.