143995-54-4

Upstream product

• 22893-78-3 2,3-di-O-acetyl-4,6-O-benzylidene-D-glucopyranose 
• 257925-66-9 acetyl 2,3-di-O-acetyl-4,6-O-benzyliden-D-glucopyranoside 
• 108031-63-6 4,6-O-benzylidene-2,3-di-O-acetyl-D-glucopyranose 

Downstream Products

• 14125-71-4 3-O-acetyl-4.6-O-benzylidene-D-arabino-hex-1-enitol 
• 74708-02-4 3-O-Acetyl-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol 

Relevant academic research and scientific papers

Facile syntheses of the trisaccharide acceptors - The key intermediates for assembling the elicitor hexasaccharide

A facile synthesis of trisaccharide 7, the key intermediate for assembling phytoalexin glucohexatose elicitor, was achieved via orthoester formation-rearrangement from stepwise coupling of 1,2-O-ethylidene-α-D- glucopyranose (2) with 2,3,4-tri-O-acetyl-6-

Photocatalytic synthesis of glycosyl bromides

Sugar hemiacetals were smoothly transformed into the corresponding glycosyl bromides by treatment with carbon tetrabromide in N,N-dimethylformamide with tris(2,2′-bipyridyl)ruthenium(II) chloride as a catalyst under visible-light irradiation. Protecting groups commonly used in carbohydrate derivatives are unaffected by the mild conditions for bromination. Georg Thieme Verlag KG Stuttgart · New York.

Rapid preparation of variously protected glycals using titanium(III)

Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)2. This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. β-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.

Convenient preparation of glycosyl bromides

Glycosyl bromides were prepared in very good yields by bromination of the corresponding anomeric hydroxyl group using a l:l mixture of triphenyl phosphite and bromine as reagent.