- 1,2-cis-β-Mannopyranoside Formation by the Dimethylphosphinothioate Method
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1,2-cis-β-Mannopyranosides were obtained predominantly by reactions of mannopyranosyl dimethylphosphinothioate derivatives with several alcohols in the presence of iodine and a catalytic amount of triphenylmethyl perchlorate as the activator in benzene.
- Yamanoi, Takashi,Nakamura, Kazumi,Takeyama, Hiroshi,Yanagihara, Kenji,Inazu, Toshiyuki
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- Visible-light-induced photoacid catalysis: Application in glycosylation with: O -glycosyl trichloroacetimidates
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The development of visible-light-induced photoacid catalyzed glycosylation is reported. The eosin Y and PhSSPh catalyst system is applied to realize glycosylation with different glycosyl donors upon light irradiation. The reaction shows a broad substrate
- Li, Juncheng,Wang, Ting,Zhao, Gaoyuan
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supporting information
p. 12659 - 12662
(2021/12/07)
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- Stereoselective synthesis of β-rhamnopyranosides via gold(i)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors
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Stereoselective β-rhamnopyranosylation remains a challenge, due to the unfavorable anomeric effect and steric hindrance of the C2-substituent; herein, this challenge is addressed with a gold(I)-catalyzed SN2-like glycosylation protocol employin
- Zhu, Yugen,Shen, Zhengnan,Li, Wei,Yu, Biao
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supporting information
p. 1536 - 1539
(2016/02/09)
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- Synthesis and glycosylation of pyrimidin-2-yl 1-thio-α-D-manno- and -α-L-rhamnopyranoside
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Pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyrano side (9), pyrimidin-2-yl 2,3,4-tri-O-benzyl-α-L-rhamnopyranoside (10), pyrimidin-2-yl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (7), and pyrimidin-2-yl 2-O-acetyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside (8) were prepared almost quantitatively from the corresponding protected 1,2-O-methoxyethylidene-β-D-manno-or-β-L-rhamnopyranose with 2-mercaptopyrimidine in the presence of mercuric bromide. Coupling reactions of the thioglycosides promoted by silver triflate with suitable glycosyl acceptors afforded 1,2-trans linked disaccharides. Copyright (C) 1998 Elsevier Science Ltd.
- Ding, Xianglan,Yang, Guangbin,Kong, Fanzuo
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p. 135 - 139
(2007/10/03)
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- New Synthetic Methods and Reagents for Complex Carbohydrates. VIII. Steroselective α- and β-Mannopyranoside Formation from Glycosyl Dimethylphosphinothioates with the C-2 Axial Benzyloxyl Group
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The reactions of mannopyranosyl dimethylphosphinothioates and alcohols using silver perchlorate as an activator in the presence of molecular sieves 4A in benzene at room temperature gave the 1,2-trans-α-mynnopyranosides in good yields.On the other hand, 1
- Yamanoi, Takashi,Nakamura, Kazumi,Takeyama, Hiroshi,Yanagihara, Kenji,Inazu, Toshiyuki
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p. 1359 - 1366
(2007/10/02)
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- Stereoselective synthesis of α-linked saccharides by use of per O-benzylated 2-pyridyl 1-thio hexopyranosides as glycosyl donors and methyl iodide as an activator
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A new, practical, stereoselective glycosidation methodology is described where per O-benzylated 2-pyridyl 1-thio-α/β-hexopyranosyl donors of D-gluco-(1), D-galacto- (2), D-manno- (3) and L-rhamno- (4) configurations have been efficiently coupled with dive
- Mereyala,Reddy
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p. 6435 - 6448
(2007/10/02)
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- A MILD GENERAL METHOD FOR THE SYNTHESIS OF α-LINKED DISACCHARIDES
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Stereoselective α-glycosylations may be achieved using stable 2-pyridyl thioglycosides (anomeric mixture) having a non-participating 2-substituent as glycosyl donor and methyl iodide as an activator.
- Reddy, G. Venugopal,Kulkarni, Vinayak R.,Mereyala, Hari Babu
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p. 4283 - 4286
(2007/10/02)
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