182412-45-9

Upstream product

• 2816-87-7 1,2-di-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose 
• 98-88-4 benzoyl chloride 
• 463-71-8 thiophosgene 
• 37614-73-6 1,2-O-isopropylidene-α-D-glucofuranose 3-O-benzoate 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 3254-32-8 6-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 66954-56-1 O⁵,O⁶-diacetyl-O³-benzoyl-O¹,O²-isopropylidene-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 182412-49-3 Benzoic acid (3aR,5S,6S,6aR)-2,2-dimethyl-5-((S)-2-oxo-[1,3]oxathiolan-5-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 124572-45-8 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 
• 182412-42-6 Benzoic acid (3aR,5S,6R,6aR)-2,2-dimethyl-5-((S)-2-oxo-[1,3]oxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 182412-41-5 3-O-benzoyl-5,6-O-carbonyl-1,2-isopropylidene-5-thio-α-D-glucofuranose 
• 37614-73-6 1,2-O-isopropylidene-α-D-glucofuranose 3-O-benzoate 
• 4105-61-7 3-O-Benzyl-5,6-didehydro-5,6-dideoxy-1,2-isopropyliden-α-D-xylo-hexofuranose 

Relevant academic research and scientific papers

Thio-sugars. IV. Synthesis of carbohydrate 1,3-glycol (six-membered) thionocarbonates and their attempted O-S rearrangement)

Four six-membered cyclic thionocarbonates (two sec-sec and two prim-sec) were prepared and their radical-promoted O-S rearrangement reaction was examined. The results revealed that the reaction in six-membered rings is difficult compared with the simple r

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.