Stereocontrolled formation of oxacephams from carbohydrates

Borsuk, Katarzyna; Kazimierski, Arkadiusz; Solecka, Jolanta; Urbańczyk‐Lipkowska, Zofia; Chmielewski, Marek

doi:10.1016/s0008-6215(02)00139-8

Cited by 17 publications

(2 citation statements)

References 21 publications

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“…Ethyl 2,3,4-Tri-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-1thio-β-D-glucopyranoside (35). The title compound was obtained from ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (34) 31 as described previously, 7 and its analytical data were the same as those reported previously.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…7 Methyl 2,3-Di-O-benzyl-4-O-(3-hydroxycarbonylpropanoyl)-6-Otriphenylmethyl-α-D-glucopyranoside (41). Succinic anhydride (350 mg, 3.50 mmol) was added to a solution of methyl 2,3-di-O-benzyl-6-O-triphenylmethyl-α-D-glucopyranoside (40, 35 539 mg, 0.88 mmol) in dry pyridine (3.0 mL), and the resulting mixture was stirred under argon for 16 h at rt. After that, the reaction mixture was concentrated under reduced pressure.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects

2016

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We previously communicated that high α-selectivity that can be achieved in intramolecular glycosylations using a rigid bisphenol A template supplemented with linkers of various lengths. Herein, we present our investigation of the mechanistic aspects of the templated synthesis that helped to design an improved template-linker combination. We demonstrate that bisphenol A as the template in combination with phthaloyl linker allows for superior stereoselectivity and yields in glycosylations. Several mechanistic studies explore origins of the enhanced stereoselectivity and yields achieved using the phthaloyl linker.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Templated Oligosaccharide Synthesis: Driving Forces and Mechanistic Aspects

2016

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Stereoselectivity in formation of oxacephams from 1,3‐alkylidene‐threitols

Borsuk¹,

Grzeszczyk²,

Szczukiewicz³

et al. 2004

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The [2+2]cycloaddition of CSI to the (Z)-propenyl ethers derived from respective 1,3-methylidene- and 1,3-ethylidene-threitols, contrary to the corresponding erythritol derivatives, is characterized by a low stereoselectivity and a lack of stereospecificity. On the other hand, the alternative method of the oxacepham formation, based on the 4-vinyloxy-azetidinone, proceeds with an excellent stereoselectivity. The CD-spectroscopy offers an attractive tool for determination of the absolute configuration of the bridgehead carbon atom at the 5-oxacepham skeleton.

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