417705-97-6

Upstream product

• 821-09-0 n-Pent-4-enyl alcohol 
• 479623-59-1 α-D-glucopyranose 1,2-(pent-4-enyl orthobenzoate) 
• 297747-11-6 (3aR,5R,6R,7S,7aR)-5-((benzoyloxy)methyl)-2-(pent-4-en-1-yloxy)-2-phenyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl dibenzoate 
• 22415-91-4 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 479623-60-4 3,4,6-tri-O-benzyl-α-D-glucopyranose 1,2-(pent-4-enyl orthobenzoate) 

Downstream Products

• 479623-70-6 benzyl 3,4,6-tri-O-benzyl-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->2)-α-D-mannopyranoside 
• 148926-02-7 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Indium(III) Iodide-Catalyzed Stereoselective Synthesis of β-Glucopyranosides by Using a Glucosyl Fluoride Donor with 2- O -Benzoyl-3,4,6-Tri- O -Benzyl Protection

We have developed a novel protocol for glucosylation by adopting a glucosyl fluoride donor with 2- O -benzoyl-3,4,6-tri- O -benzyl protection. The protocol is useful for the ready assembly of β-linked functional glycoconjugates, and the reaction accommodates a broad range of substrates. Conveniently, water-tolerant and commercially available InI 3 is used as a catalyst, and no other additional reagent is required. The method involves an interesting process for glucosyl fluoride activation and, in particular, permits the stereoselective construction of partially benzylated glucopyranosides carrying a selectively removable 2- O -benzoyl group, which hold great potential as glycosyl receptors for building further 1,2-glycosidic linkages.

Orthoester-based strategy for efficient synthesis of the virulent antigenic-1,2-linked oligomannans of Candida albicans

Orthobenzoates of glucose and mannose provide donor and acceptor partners to produce a disaccharide bearing a benzoyl group at the site where gluco to manno conversion is required, the inverted center being ready to function, iteratively, as the next acce

Comparing n-pentenyl orthoesters and n-pentenyl glycosides as alternative glycosyl donors

As is well known, cyclic 1,2-glycosyl orthoesters undergo ready acid catalyzed rearrangement to 2-O-acyl glycosides in which the alkoxy group is transferred from the orthoester to the anomeric center in a highly stereocontrolled process. The related n-pentenyl derivatives are unique in that either the orthoester (NPOE) or its rearrangement product (NPGAC) can function as a glycosyl donor, and mechanistic considerations indicate that both should (or could!) lead to the same product(s) arising from trans-orthoesterification, glycosidation, glycosyl esterification, etc. Experiments are described which show that the product obtained from a given reaction can be optimized by careful choice of the donor, NPOE or related NPGAC, and careful attention to reaction conditions, electrophilic promoter, 'size' of the glycosyl acceptor, and experimental protocol.