29364-56-5

Upstream product

• 253328-56-2 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose 
• 108-24-7 acetic anhydride 
• 108-22-5 Isopropenyl acetate 
• 50-99-7 D-glucose 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 19684-32-3 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose 
• 7284-07-3 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 
• 75-36-5 acetyl chloride 

Downstream Products

• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 68095-73-8 3,5-Di-O-acetyl-1,2-O-isopropyliden-6-O-trityl-α-D-glucofuranose 
• 35919-95-0 O⁴,O⁵,O⁶-tribenzoyl-S²,S³-diethyl-D-2,3-dithio-allose diethyl dithioacetal 
• 253328-56-2 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose 
• 192717-86-5 (4-nitro)phenyl β-D-glucofuranoside 
• 33737-08-5 1,2-O-isopropylidene-6-O-trityl-α-D-glucofuranoside 

Relevant academic research and scientific papers

Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions

A fast and efficient acylation of carbohydrate derivatives and free sugars using a stoichiometric quantity of acylating agents in the presence of sulfamic acid, an environmentally benign catalyst, under organic solvent-free conditions is reported. Excellent yields in the selective acylation and sulfation of carbohydrate derivatives have also been achieved using sulfamic acid as the catalyst. The reaction is fast and the yields were excellent.

A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)3·xH2O

The transformation of acetonides into the corresponding diacetates is often required in the synthetic chemistry. An efficient procedure for direct conversion of acetonides into diacetates in the presence of Bi(OTf)3·xH2O under mild c

Tandem acetalation-acetylation of sugars and related derivatives with enolacetates under solvent-free conditions

(Chemical Equation Presented) Molecular iodine catalyzes acetalation and acetylation of reducing sugars and sugar glycosides with stoichiometric amounts of enol acetates under solvent-free conditions, thereby facilitating the synthesis of various types of orthogonally protected sugar derivatives in short time and good yields. The outcome of the reaction can be controlled by variation in temperature. Thus at lower temperature, it is possible to obtain the acetonide acetate as a single product whereas peracetate is the major product at higher temperature.

Acylation of carbohydrates over Al2O3: Preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides

Selective and per-O-acylation of carbohydrate derivatives using acyl chlorides and Al2O3, a solid support reagent, is reported. This protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)3

Bi(OTf)3-catalyzed acylation of alcohols with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)3/acid anhydride protocol was so powerful that sterically demanding or tertiary alcohols could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technology was developed in order to overcome difficulty in separation of the acylated product from the remaining acylating reagent: methanolysis of the unreacted anhydride into easily separable methyl ester realized quite easy separation of the desired acylation product. The Bi(OTf)3/acid anhydride protocol was applicable to a wide spectrum of alcohols bearing various functionalities. Acid-labile THP- or TBS-protected alcohol, furfuryl alcohol, and geraniol could be acylated as well as base-labile alcohols. Even acylation of functionalized tertiary alcohols was effected at room temperature.

The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides

Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.

Virtual 1H-1H spin-spin coupling in a linear five-spin system on the pyranose rings of some glucuronides

In the 1H NMR spectra of methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate-(1 -> 3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (6) and methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate-(1 -> 6)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose (7), which were obtained by the reaction of 1,2;5,6-di-O-isopropylidene-α-D-glucofuranose (1) with methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyluronate bromide (5) in the presence of Hg(CN)2 in 1:1 benzene-nitromethane at 45 deg C, protons on both β-D-glucopyranosyluronate rings were observed as very complex signals that could not be interpreted by first-order analysis.Similar complex signals were also observed for the protons on the β-D-glucopyranosyluronate rings that were sugar components of some triterpenoidal glycosides (13-15).These complex signals were determined to be due to virtual long-range spin-spin coupling in the linear five-spin system on the glucopyranosyluronate rings of the glucuronides by 1H, 13C, H-C COSY, 1D HOHAHA, and spin-simulation spectroscopies.

Regioselective mono-oxidation of Non-protected carbohydrates by brominolysis of the tin intermediates

Most of the glycosides examined were smoothly oxidized by the bis-tributyltin oxide-bromine method without protection of the other hydroxyl groups to the mono-oxo derivatives in high yield and with high regioselectivity.The regioselectivity (position of oxidation) can be predicted from two independent rules: anomeric control (the oxidation takes place at C-3 for the glycosides which have an equatorial glycosidic linkage and at C-4 for those which have an axial glycosidic linkage) and axial oxidation for cis-1,2 glycols.Keywords - carbohydrate; glycoside; oxidation; regioselective oxidation; bis-tributyltin oxide-bromine; dibutyltin oxide-bromine; brominolysis; oxo-glycoside; 13C-NMR.