29364-56-5

Basic information

• Product Name: 1-O,2-O-Isopropylidene-α-D-glucofuranose 3,5,6-triacetate
• Synonyms: 1-O,2-O-(1-Methylethylidene)-α-D-glucofuranose 3,5,6-triacetate;1-O,2-O-Isopropylidene-α-D-glucofuranose 3,5,6-triacetate
• CAS NO: 29364-56-5
• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.32978
• Mol File: 29364-56-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-O,2-O-Isopropylidene-α-D-glucofuranose 3,5,6-triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O,2-O-Isopropylidene-α-D-glucofuranose 3,5,6-triacetate(29364-56-5)
• EPA Substance Registry System: 1-O,2-O-Isopropylidene-α-D-glucofuranose 3,5,6-triacetate(29364-56-5)

Safety Data

• Hazardous Substances Data: 29364-56-5(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 33737-08-5 1,2-O-isopropylidene-6-O-trityl-α-D-glucofuranoside 
• 192717-86-5 (4-nitro)phenyl β-D-glucofuranoside 
• 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 

Relevant articles and documents

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.

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.

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.