4105-61-7

Usage

Chemical class

Glucopyranoses

Derivative of

Glucose

Attached groups

Benzoyloxy group on the third carbon, isopropylidene group on the first and second carbons

Common use

Protecting group for hydroxyl groups in glucose

Application

Organic synthesis and carbohydrate chemistry

Structure

Valuable building block for the synthesis of complex carbohydrate molecules

Derivatives

Often used in the production of pharmaceuticals and natural products
These properties and contents provide a comprehensive overview of 1,2-O-Isopropylidene-3-benzoyloxy-5,6-dideoxy-glucofuranose, highlighting its chemical structure, applications, and significance in the field of organic synthesis and carbohydrate chemistry.

InChI:InChI=1/C16H18O5/c1-4-11-12(13-15(19-11)21-16(2,3)20-13)14(17)18-10-8-6-5-7-9-10/h4-9,11-13,15H,1H2,2-3H3/t11-,12+,13?,15?/m1/s1

Upstream product

• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 2816-87-7 1,2-di-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose 
• 37614-73-6 1,2-O-isopropylidene-α-D-glucofuranose 3-O-benzoate 
• 182412-45-9 Benzoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-((R)-2-thioxo-[1,3]dioxolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Downstream Products

• 37614-73-6 1,2-O-isopropylidene-α-D-glucofuranose 3-O-benzoate 

Relevant academic research and scientific papers

Expeditious synthesis of enantiopure symmetrical macroheterocycles by ring-closing metathesis of ether and tether-linked 1,2-O- isopropylidenefuranosides

Bis-olefinic symmetrical carbohydrate derivatives were prepared by joining two 1,2-O-isopropylidenefuranose units either through an ether linkage or by a tether of variable size. The ring-closing metathesis (RCM) of these substrates using Grubbs' first-ge

Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: Synthesis of 5-thioglucose

The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2, when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other hand, thermolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.