Chemical Synthesis of a Tetrasaccharide Fragment Related to the Exopolysaccharide ofArthrobacter sp. CE-17

Lemanski, Gregor; Ziegler, Thomas

doi:10.1002/(sici)1099-0690(200001)2000:1<181::aid-ejoc181>3.0.co;2-7

Cited by 12 publications

(1 citation statement)

References 29 publications

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“…A known phenyl 4,6‐O‐benzylidene‐1‐thio‐β‐ d ‐glucopyranoside 7 [19] was selectively benzoylated (method A ) to give a mixture of 3‐ O ‐ and 2‐ O ‐benzoylated derivatives 8 [20] and 9 (63 %), the ratio of 8 : 9 was 7 : 1 according to NMR data. The mixture of 8 + 9 was silylated (method B ) to afford a mixture of 1 + 10 followed by removal of 4,6‐ O ‐benzylidene group under acidic conditions (method D ) to give diols 13 (63 %) and 14 (13 %).…”

Section: Resultsmentioning

confidence: 99%

Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐cis‐Glucosylation

et al. 2022

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Glycosylation with phenyl 3,4,6-tri-O-benzoyl-2-O-triisopropylsilyl (TIPS)-1-thio-β-d-glucopyranoside is highly 1,2-cis-stereoselective, while the use of 2,3-di-O-TIPS glucosyl donor with benzoyl groups at O-4 and O-6 results in the loss of α-stereoselectivity (α/β = 3 : 1). Complete α-stereocontrol with 2-O-TIPS substituted glucosyl donors could only be achieved in glucosylation of weak nucleophiles. In this case, the glucosylation seems to proceed along the S N 1-like pathway via the 4 H 3 conformer of glycosyl cation stabilized by the bulky TIPS group at O-2.

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Section: Resultsmentioning

confidence: 99%

Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐cis‐Glucosylation

et al. 2022

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Other Methods for Glycoside Synthesis: Sections 5.3 and 5.4

Toshima

Ziegler

2008

Handbook of Chemical Glycosylation

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Synthesis of Pentasaccharide Fragments Related to the O‐Specific Polysaccharide of Shigella flexneri Serotype 1a

Lemanski

Ziegler

2006

Eur J Org Chem

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The synthesis of the pentasaccharide 5‐aminopentylglycosides α‐L‐Rhap‐(1→3)‐[α‐D‐Glcp‐(1→4)]‐β‐D‐GlcpNAc‐(1→2)‐α‐L‐Rhap‐(1→2)‐α‐L‐Rhap‐1‐O‐(CH2)5NH2 (29) andα‐L‐Rhap‐(1→3)‐α‐L‐Rhap‐(1→3)‐[α‐D‐Glcp‐(1→4)]‐β‐D‐GlcpNAc‐(1→2)‐α‐L‐Rhap‐1‐O‐(CH2)5NH2 (28), related to the O‐specific polysaccharide of Shigella flexneri serotype 1a by coupling of the suitably protected trisaccharides α‐D‐Glcp‐(1→4)‐β‐D‐Glcp(1→2)‐α‐L‐Rhap‐1‐O‐(CH2)5NH2 (23) and α‐L‐Rhap‐(1→3)‐[α‐D‐Glcp‐(1→4)]‐β‐D‐Glcp‐1‐SPh (26) with the corresponding rhamnosyl glycosides α‐L‐Rhap‐(1→3)‐α‐L‐Rhap‐1‐SEt (17) and α‐L‐Rhap‐(1→3)‐α‐L‐Rhap‐1‐O‐(CH2)5NH2 (13), is described. Building blocks 23 and 26 were prepared by intramolecular glycosylation of an unsymmetrically tethered cellobiosamine derivative. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Chemical Synthesis of a Tetrasaccharide Fragment Related to the Exopolysaccharide ofArthrobacter sp. CE-17

Cited by 12 publications

References 29 publications

Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐cis‐Glucosylation

Stereocontrolling Effect of a Single Triisopropylsilyl Group in 1,2‐cis‐Glucosylation

Other Methods for Glycoside Synthesis: Sections 5.3 and 5.4

Synthesis of Pentasaccharide Fragments Related to the O‐Specific Polysaccharide of Shigella flexneri Serotype 1a

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