26623-13-2

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 329899-64-1 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 131289-34-4 3,5,6-tri-O-benzoyl-1,2-O-isopropylidene-β-L-idofuranose 
• 131289-33-3 6-O-acetyl-3-O-benzoyl-1,2-O-isopropylidene-5-O-p-nitrobenzoyl-β-L-idofuranose 
• 131289-32-2 3-O-benzoyl-6-bromo-6-deoxy-1,2-O-isopropylidene-5-O-p-nitrobenzoyl-β-L-idofuranose 
• 108802-08-0 3,5-di-O-benzoyl-6-bromo-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 72733-12-1 5.6-Di-O-benzoyl-3-O-benzyl-1.2-O-isopropyliden-β-L-idofuranose 
• 22331-19-7 3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 29747-91-9 1,2-O-isopropylidene-β-L-idofuranose 
• 87357-54-8 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose 

Downstream Products

• 1374991-66-8 tert-butyldiphenyl(((3aR,5S,6R,6aR)-2,2,6-trimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)methoxy)silane 
• 1357178-65-4 1,2-O-isopropylidene-3-C-phenyl-5-azido-α-D-ribofuranose 
• 1357178-64-3 1,2-O-isopropylidene-3-C-phenyl-5-O-tosyl-α-D-ribofuranose 
• 237412-43-0 1,2-O-isopropylidene-3-C-phenyl-α-D-ribofuranose 
• 1043894-82-1 C₁₄H₁₆O₅ 
• 1357178-75-6 1,2-O-isopropylidene-3-C-phenyl-5-(4-(3-aminophenyl)-1H-1,2,3-triazole-1-yl)-a-D-ribofuranose 
• 1357178-74-5 1,2-O-isopropylidene-3-C-phenyl-5-(4-phenyl-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose 
• 1357178-73-4 1,2-O-isopropylidene-3-C-phenyl-5-(4-(2-hydroxypropan-2-yl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose 
• 1357178-72-3 1,2-O-Isopropylidene-3-C-phenyl-5-(4-(3-chloropropyl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose 
• 1357178-71-2 1,2-O-isopropylidene-3-C-phenyl-5-(4-cyclohex-1-en-1-yl-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose 
• 1357178-70-1 1,2-O-isopropylidene-3-C-phenyl-5-(4-(2-hydroxy-4-methylpentan-2-yl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose 
• 1357178-69-8 1,2-O-isopropylidene-3-C-phenyl-5-(4-(tetrahydro-2H-pyran-2-yloxymethyl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose 
• 1357178-68-7 1,2-O-isopropylidene-3-C-phenyl-5-(4-(hydroxymethyl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose 
• 1357178-67-6 1,2-O-isopropylidene-3-C-phenyl-5-(4-(phenoxymethyl)-1H-1,2,3-triazole-1-yl)-α-D-ribofuranose 

Relevant academic research and scientific papers

PYRIDINIUM DICHROMATE OXIDATION. MODIFICATION ENHANCING ITS SYNTHETIC UTILITY.

An improved procedure is described for extremly rapid and efficient oxidation of alcohols, by adding a small quantity of anhydrous acetic acid (AcOH) to pyridinium dichromate (PDC) and freshly activated molecular sieve powder in CH2Cl2 at room temperature.

COMPOUNDS FOR THE TREATMENT OF SYSTEMIC INSULIN RESISTANCE DISORDERS AND THE USE THEREOF

Aspects of the invention relate to novel synthetic compounds for treatment of metabolic diseases partially associated with systemic insulin resistance caused by Galectin proteins binding and inhibiting insulin and TGFb1 receptors causing physiological disturbances in the insulin pathways.

A carbohydrate approach for the formal total synthesis of the prostacyclin analogue (16S)-iloprost

The formal total synthesis of the synthetic and stable analogue of prostacyclin, (16S)- iloprost is described via a convergent synthesis starting from readily available d-glucose. Julia olefination and the aldol reaction are the key steps involved in the synthesis.

Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases

Ten new 1,2,3-triazole glycoconjugates were synthesized from d-glucose and evaluated in in vitro assays for their ability to inhibit the enzyme α-glucosidase. Most of the compounds had low activity or were inactive when compared with acarbose. However, the derivative 1,2-O-isopropylidene-3- phenyl-5-(4-phenyl-1H-1,2,3-triazole-1-yl)-α-d-ribofuranose (19i) possessed activity comparable with the standard drug. The influence of the phenyl group on carbon 3 of the carbohydrate framework is discussed.

Triethylammonium fluorochromate - A new, mild, stable, and inexpensive chromium(VI) oxidant

Triethylammonium fluorochromate was prepared and was used to quantitatively oxidize a number of organic substrates. Triethylammonium fluorochromate is a versatile reagent ensuring effective and selective oxidation of organic compounds, in particular of alcohols, under mild conditions.

Biologically potent L-hexoses and 6-deoxy-L-hexoses: Their syntheses and applications

This account describes our recent work in the development of new methodologies to prepare rare and biologically potent L-hexoses and 6-deoxy-L-hexoses, from cheapest D-glucose, via L-hexofuranoses and 1,6-anhydro-β-L-hexopyranoses as key building blocks. Their applications in the syntheses of heparin oligosaccharides, the carbohydrate moiety of bleomycin A2, and L-acovenose are also summarized here.

From D-Glucose to Biologically Potent L-Hexose Derivatives: Synthesis of α-L-Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate

A novel and convenient route for the synthesis of biologically potent and rare L-hexose derivatives from D-glucose is described. Conversion of diacetone-α-D-glucose (14) into 1,2:3,5-di-O-isopropylidene-β -L-idofuranose (19) was efficiently carried out in two steps. Orthogonal isopropylidene rearrangement of compound 19 led to 1,2:5,6-di-O-isopropylidene-β-L-idofuranose (27), which underwent regioselective epimerization at the C3 position to give the L-talo- and 3-functionalized L-idofuranosyl derivatives. Hydrolysis of compound 19 under acidic conditions furnished 1,6-anhydro-β-L-idopyranose (35) in excellent yield, which was successfully transformed into the corresponding L-allo, L-altro, L-gulo, and L-ido derivatives via regioselective benzylation, benzoylation, triflation and nucleophilic substitution as the key steps. Applications of these 1,6-anhydro-β-L-hexopyranoses as valuable building blocks to the syntheses of 4-methylcoumarin-7-yl-α-L-iduronic acid and the disaccharide moieties of bleomycin A2 as well as heparan sulfate are highlighted.

Efficient synthesis of L-altrose and L-mannose

Two convenient routes for the synthesis of L-altrose and L-mannose from 1,2:3,5-di-O-isopropylidene-β-L-idofuranose in four and six steps via the stereoselective hydroboration and hydrogenation of olefins as key steps are described here, respectively. (C) 2000 Elsevier Science Ltd.

Synthesis and reactions of chlorodeoxy-L-talofuranoid derivatives

Reaction of 6-O-acyl-3,5-O-benzylidene derivatives of 1,2-O-isopropylidene-α-D-glucofuranose with N-bromosuccinimide affords mainly 5-O-acyl-6-bromo-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose in good yield.Convenient preparative routes to 1,2-O-isopropylidene-β-L-talofuranose and its conversion into 5-chloro-5-deoxy and 5,6-dichloro-5,6-dideoxy derivatives are described.

INTRODUCTION OF gem-DIALKYL GROUP TO HEXOFURANOSE BY ORTHO ESTER CLAISEN REARRANGEMENT

The ortho ester Claisen rearrangement of D-ribo- or L-lyxo-hexofuranose derivative which possesses an allyl alcohol functionality on C-3, proceeds stereoselectively to give a 3-C-dialkylated product.The stereochemistry of a newly introduced quaternary center of the product was unambiguously established by a chemical modification.