Development of a Novel Sugar Linkage: 6,6′‐Ether‐Connected Sugars

Takahashi, Hideyo; Fukuda, Toshimitsu; Mitsuzuka, Haruhiko; Namme, Rie; Miyamoto, Hidetoshi; Ohkura, Yasufumi; Ikegami, Shiro

doi:10.1002/anie.200352388

Cited by 20 publications

(15 citation statements)

References 17 publications

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“…We have therefore investigated a novel synthesis of 6,6¢ether-linked pyranoses through an acetalization-reduction procedure. 3 While this approach was successfully applied to the synthesis of various new ether-linked sugars, 4 we continued to examine an alternative method by which an ether linkage could be introduced at other positions of pyranoses. Herein, we describe a new synthesis of etherlinked sugar by regiospecific nucleophilic opening of carbohydrate oxiranes.…”

Section: Figurementioning

confidence: 99%

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Synthesis of Ether-Linked Sugar by Nucleophilic Opening of Carbohydrate Oxiranes

Nishiyama¹,

Nakayama²,

Natsugari³

et al. 2008

Synthesis

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A new synthesis of ether-linked sugar utilizing the nucleophilic ring-opening reaction of carbohydrate a-or b-oxirane was developed. The reaction of 2,3-anhydro-a-D-mannopyranosides resulted in the expected high regioselectivity. In contrast, 2,3-anhydro-a-D-allopyranosides showed an unusual regioselectivity shift. The differentiating properties of carbohydrate a-or b-oxirane were investigated by comparing various conditions of the reaction.

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Section: Figurementioning

confidence: 99%

“…The ring-opening reaction of carbohydrate oxirane with strong anionic nucleophiles (e.g., N 3 -) has been investigated with great interest. 8 However, the use of weakly nucleophilic reagents has not been fully established.…”

Section: Figurementioning

confidence: 99%

Synthesis of Ether-Linked Sugar by Nucleophilic Opening of Carbohydrate Oxiranes

Nishiyama¹,

Nakayama²,

Natsugari³

et al. 2008

Synthesis

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“…[24] Recently, the formation of glycosylidene acetals and their selective reduction for the formation of coyolosa, a 6,6Ј-ether linked disaccharide natural product, has been reported. [25] …”

Section: Introductionmentioning

confidence: 97%

Synthesis of a New Type of Glycosidic Linkage: Acetal‐Linked Disaccharides and Trisaccharides of Acyclic and Cyclic Sugars

Madhusudan

Misra

2005

Eur J Org Chem

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New types of di-and trisaccharides related to a unique trisaccharide present in the cell walls of Proteus have been synthesized by coupling of acyclic sugar dithioacetals and di-and monohydroxy cyclic sugars. In this class of compounds an acyclic sugar is linked to a cyclic sugar through an acetal linkage. The formation of these acetal-linked pseudodi-and -trisaccharides has been achieved by a generalized reaction

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“…Vasella et al aimed at C -mannosides, replacing the anomeric oxygen by a methylene group, and prepared analogues 4 [ 12 ] and 5 [ 13 ] ( Figure 1 ). We also considered the guanofosfocin analogue 6 of interest, in analogy to other, stable ether-linked pseudo-disaccharides [ 14 , 15 , 16 ] and report a synthesis of this ether-linked pseudo-disaccharide containing an 8-alkylated guanine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine

2013

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The synthesis of stable guanofosfocin analogues has attracted considerable attention in the past 15 years. Several guanofosfocin analogues mimicking the three constitutional elements of mannose, ribose, and guanine were designed and synthesized. Interest in ether-linked pseudodisaccharides and 8-alkylated guanines is increasing, due to their potential applications in life science. In this article, a novel guanofosfocin analogue 6, an ether-linked pseudodisaccharide connected α-C-glycosidically to an 8-alkylated guanine, was synthesized in a 10-longest linear step sequence from known diol 13, resulting in an overall yield of 26%. The key steps involve the ring-opening of cyclic sulfate 8 by alkoxide generated from 7 and a reductive cyclization of 4-N-acyl-2,4-diamino-5-nitrosopyrimidine 19 to form compound 6.

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Development of a Novel Sugar Linkage: 6,6′‐Ether‐Connected Sugars

Cited by 20 publications

References 17 publications

Synthesis of Ether-Linked Sugar by Nucleophilic Opening of Carbohydrate Oxiranes

Synthesis of Ether-Linked Sugar by Nucleophilic Opening of Carbohydrate Oxiranes

Synthesis of a New Type of Glycosidic Linkage: Acetal‐Linked Disaccharides and Trisaccharides of Acyclic and Cyclic Sugars

Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine

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