469-90-9

Usage

Chemical Properties

White powder

InChI:InChI=1/C7H12O6/c8-2-7-6(11)5(10)4(9)3(13-7)1-12-7/h3-6,8-11H,1-2H2/t3-,4-,5-,6+,7-/m1/s1

Upstream product

• 625-48-9 2-nitro-1-ethanol 
• 50-69-1 D-ribose 
• 100816-37-3 hexa-O-acetyl-keto-D-altro-[2]heptulose 
• 3019-74-7 sedoheptulose 

Downstream Products

• 122272-65-5 O¹-Trityl-β-D-altro-2,7-anhydro-[2]heptulopyranose 
• 120857-20-7 Tetra-O-benzoyl-β-D-altro-2,7-anhydro-[2]heptulopyranose 
• 2893-25-6 tetrakis-O-(toluene-4-sulfonyloxy)-β-D-altro-2,7-anhydro-[2]heptulopyranose 
• 119621-95-3 O¹-Trityl-β-D-altro-2,7-anhydro-[2]heptulofuranose 
• 119949-43-8 O³,O⁴,O⁵-Tribenzoyl-O¹-trityl-β-D-altro-2,7-anhydro-[2]heptulopyranose 
• 121292-32-8 tetrakis-O-(toluene-4-sulfonyl)-β-D-altro-2,7-anhydro-[2]heptulofuranose 
• 77270-45-2 2,7:3,4-di-O-<(4-methoxyphenyl)ethylidene>sedoheptulosan 

Relevant academic research and scientific papers

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.

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.