Synthesis of : Sugar moiety of antitumor antibiotic bleomycin

Oshitari, Tetsuta; Shibasaki, Masakatsu; Yoshizawa, Takeshi; Tomita, Masahiro; Takao, Ken Ichi; Kobayashi, Susumu

doi:10.1016/s0040-4020(97)00360-8

Cited by 70 publications

(54 citation statements)

References 26 publications

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“…Anomeric mixtures of tetra- O -benzyl- d -mannopyranosyl acetate 1α,β and 2,3-di- O -benzyl-4,6- O -benzylidene- d -mannopyranosyl acetate 2α,β (Fig 2) were prepared and separated into the constituent anomers as described in the literature. 44,45 The corresponding 3- O -benzoyl analogs 3α,β and 4α,β were prepared as outlined in Scheme 1 from the thioglycosides 6 , obtained from the alcohol 5 , 46 and 7 47 by hydrolysis of the thioglycoside function with N -bromosuccinimide and aqueous acetone, and acetylation.…”

Section: Resultsmentioning

confidence: 99%

Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series

Sharma¹,

Bohé²,

Crich³

2012

Carbohydrate Research

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It is reported that the replacement of the 4- and 6-O-benzyl ethers in 2,3,4,6-tetra-O-benzyl-α,β-mannopyranose by a 4,6-O-benzylidene acetal results in an increased population of the β-anomer at equilibrium in CDCl3 solution. The phenomenon is considered to arise from the lower steric bulk of the benzylidene acetal that, through diminished buttressing interactions, reduces steric interactions normally present in the β-anomer.

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Section: Resultsmentioning

confidence: 99%

Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series

Sharma¹,

Bohé²,

Crich³

2012

Carbohydrate Research

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“…Benzylation of compound 5 with benzyl bromide and NaH in DMF gave the purified benzyl ether 6 in 53% yield over three steps. The compound 6 was treated with N –bromosuccinimide (NBS) to afford the resulting lactol, 18 which was converted into the corresponding trichloroacetimidate 7 using trichloroacetonitrile and 1,8–diazabicycloundec–7–ene (DBU) in 68% yield over two steps.…”

Section: Resultsmentioning

confidence: 99%

Chemical synthesis of the outer core oligosaccharide of Escherichia coli R3 and immunological evaluation

Shang

Xiao

et al. 2015

Org. Biomol. Chem.

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Lipopolysaccharides (LPS), major virulence determinants in Gram–negative bacteria, are responsible for many pathophysiological responses and can elicit strong immune responses. In order to better understand the role of LPS in host–pathogen interactions and elucidate the immunogenic properties of LPS outer core oligosaccharide, an all α–linked Escherichia coli R3 outer core pentasaccharide was first synthesized with a propyl amino linker at the reducing end. This oligosaccharide was also covalently conjugated to a carrier protein (CRM197) via the reducing end propyl amino linker. An immunological analysis demonstrated that this glycoconjugate can elicit specific anti-pentasaccharide antibodies with in vitro bactericidal activity. These findings will contribute to further exploring this pentasaccharide antigen as a vaccine candidate.

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“…For the synthesis of the monosaccharide building block 6, known intermediate 12 19 was used (Scheme 3). Dibutyltin oxide-mediated selective benzylation of the diol 12 afforded C-3 benzyl ether 13 in 85% yield.…”

Section: Resultsmentioning

confidence: 99%

Improved Synthesis of the Tetrasaccharide Repeat Unit of the O-Antigen Polysaccharide from Escherichia coli O77

Lee¹,

Baek²,

Jeon³

et al. 2007

Bulletin of the Korean Chemical Society

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The efficient synthesis of a tetrasaccharide, the suitably protected form of the repeat unit,of the O-antigen polysaccharide of the lipopolysaccharide from E. coli O77 has been accomplished. Glycosylation reactions for the coupling of four monosaccharide building blocks of the tetrasaccharide were carried out employing the CB glycoside method, the mannosyl 4-pentenoate/PhSeOTf method, and the glycosyl trichloroacetimidate method with complete stereoselectivities in excellent yields.

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Synthesis of : Sugar moiety of antitumor antibiotic bleomycin

Cited by 70 publications

References 26 publications

Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series

Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series

Chemical synthesis of the outer core oligosaccharide of Escherichia coli R3 and immunological evaluation

Improved Synthesis of the Tetrasaccharide Repeat Unit of the O-Antigen Polysaccharide from Escherichia coli O77

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