3343-95-1

Upstream product

• 3019-74-7 sedoheptulose 

Downstream Products

• 591-49-1 1-methylcyclohex-1-ene 
• 6893-84-1 Hepta-O-acetyl-L-glycero-D-glucoheptit 
• 6893-84-1 D-glycero-D-gluco-heptitol hepta acetate 
• 5345-81-3 O³,O⁵-((s)-benzylidene)-D-glycero-D-gulo-heptitol 
• 6893-84-1 meso-glycero-ido-heptitol acetate 
• 6893-84-1 Acetic acid (1R,2R,3S)-2,3,4-triacetoxy-1-((1S,2S)-1,2,3-triacetoxy-propyl)-butyl ester 
• 4141-44-0 O¹,O³;O⁵,O⁷-((Ξ,Ξ)-dibenzylidene)-L-glycero-L-galacto-heptitol 
• 654-29-5 L-allo-1,3,4,5,6,7-Hexahydroxy-heptan-2-on 
• 654-29-5 DL-gluco-1,3,4,5,6,7-Hexahydroxy-heptan-2-on 
• 3624-30-4 L-gluco-[2]heptosulose-bis-phenylhydrazone 
• 6893-84-1 1,2,3,4,5,6,7-heptaacetoxy-heptane 
• 7510-98-7 L-(1R)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-xylitol 
• 3624-30-4 L-gulo-[2]heptosulose-bis-phenylhydrazone 

Relevant academic research and scientific papers

Organocatalytic Synthesis of Higher-Carbon Sugars: Efficient Protocol for the Synthesis of Natural Sedoheptulose and d-Glycero-l-galacto-oct-2-ulose

Herein we report a short and efficient protocol for the synthesis of naturally occurring higher-carbon sugars—sedoheptulose (d-altro-hept-2-ulose) and d-glycero-l-galacto-oct-2-ulose—from readily available sugar aldehydes and dihydroxyacetone (DHA). The key step includes a diastereoselective organocatalytic syn-selective aldol reaction of DHA with d-erythrose and d-xylose, respectively. The methodology presented can be expanded to the synthesis of various higher sugars by means of syn-selective carbon–carbon-bond-forming aldol reactions promoted by primary-based organocatalysts. For example, this methodology provided useful access to d-glycero-d-galacto-oct-2-ulose and 1-deoxy-d-glycero-d-galacto-oct-2-ulose from d-arabinose in high yield (85 and 74 %, respectively) and high stereoselectivity (99:1).

Four orders of magnitude rate increase in artificial enzyme-catalyzed aryl glycoside hydrolysis

(6A6DR)-6A,6D-Di-C-cyano- β-cyclodextrin (1) and 6A,6D-di-C-cyano-α- cyclodextrin (2) were synthesized and shown to catalyze hydrolysis of aryl glycosides into glucose and phenol with a reaction following Michaelis-Menten kinetics. At pH 8.0 and 59 °C hydrolysis of 4-nitrophenyl α-glucopyranoside was catalyzed by 1 with KM = 10.5 ± 1.5 mM, kcat = 1.42(±0.09) × 10-4 s -1 and kcatk/uncat = 7922, Catalysis was observed with a concentration of 1 as low as 10 μM. Hydrolysis of the other aryl glycosides containing stereochemical variation in the sugar-moiety and 4-nitro-, 2-nitro-, 2-aldehydo-, and 2,4-dinitro- were also catalyzed by 1 and 2 with kcat/kuncat ranging from 4 to 7100. Hydrolysis of a phenyl β-D-glucoside or the thioglycoside tolylthio β-D-glucoside was also catalyzed. From a series of prepared analogues of 1 it was found that the catalysis was associated with the hydroxyl groups α to the nitril groups. The monocyanohydrin 6-C-cyano-β-cyclodextrin (3) was also found to catalyze the hydrolysis of 4-nitrophenyl β-glucopyranoside with k Cat/kuncat = 1356. It was proposed that the cyclodextrin cyanohydrins 1-3 catalyze the hydrolysis by general acid catalysis on the bound substrate.