phenyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside | 126113-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside
• 英文别名: (2R,3S,4R,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)-2-phenylsulfanyloxane-3,4-diol
• CAS: 126113-70-0
• 化学式: C₂₆H₂₈O₅S
• 分子量: 452.571
• InChiKey: NSSPYKLQGZRHTI-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 phenyl 2,4,6-tri-O-benzyl-3-O-(3-carboxypropanoyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

  DOI：

  10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u
• 作为产物：
  描述：

  苯基1-硫代吡喃己糖苷 在 咪唑 、 四丁基氟化铵 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 phenyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  摘要：

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.

  DOI：

  10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u

文献信息

• Synthetic and immunological studies of <i>Salmonella</i> Enteritidis O-antigen tetrasaccharides as potential anti-<i>Salmonella</i> vaccines
  作者：Chang-Xin Huo、Debashis Dhara、Scott M. Baliban、Setare Tahmasebi Nick、Zibin Tan、Raphael Simon、Anup Kumar Misra、Xuefei Huang

  DOI：10.1039/c8cc08622b

  日期：——

  The conjugate of a synthetic Salmonella Enteritidis tetrasaccharide with bacteriophage Qβ induced powerful anti-glycan IgG responses for complete protection from lethal challenges of bacteria.

  合成的沙门氏菌Enteritidis四糖与噬菌体Qβ的结合诱导了强大的抗糖基IgG反应，从而完全保护免受细菌致命挑战。
• Synthesis and Photochromic Properties of Azobenzene-Derived Glycomacrolactones
  作者：Chaoqi Lin、Stéphane Maisonneuve、Cyril Theulier、Juan Xie

  DOI：10.1002/ejoc.201801832

  日期：2019.2.28

  Photoswitchable and bistable glycomacrolactones: Azobenzene‐based glycomacrolactones have been synthesized from gluco and manno thioglycosides. These glycoazobenzenes display excellent photochromic properties and bistability. The E→Z photoisomerization induced a large change in the conformation and the chirality of the macrolactones. Both E‐ and Z‐glycomacrolactones show a (P) helical structure, as

  光开关和双稳态的糖基内酯：基于偶氮苯的糖基内酯是由葡萄糖和甘露糖基硫代糖苷合成的。这些糖基偶氮苯具有出色的光致变色性能和双稳性。该ê → ž光致异构引起的构象变化较大和大环内酯的手性。既ë -和Ž -glycomacrolactones示出了（P）螺旋结构，通过TD-DFT计算所建议的。
• Superbase-Catalyzed Stereo- and Regioselective Glycosylation with 2-Nitroglycals: Facile Access to 2-Amino-2-deoxy-<i>O</i>-glycosides
  作者：Kumar Bhaskar Pal、Aoxin Guo、Mrinmoy Das、Gábor Báti、Xue-Wei Liu

  DOI：10.1021/acscatal.0c00753

  日期：2020.6.19

  An efficient superbase-catalyzed stereo- and regioselective glycosylation of 2-nitroglycals with high functional group compatibility is reported. The ion pair generated from alcohol and a catalytic amount of P-4-t-Bu was vital for the successful implementation of this stereoselective glycosylation under mild conditions, producing moderate to good yields. Under reported reaction conditions, 2-nitrogalactals produce alpha-stereoisomers exclusively, while 2-nitroglucal yielded more beta-products. The notable difference between the outcomes was investigated by the density functional theory (DFT) study. In addition, we have synthesized the key intermediate of a mucin-type core-6 glycoconjugate, thus illustrating the synthetic potency of this method.
• Facile construction of 1,2-cis glucosidic linkage using sequential oxidation–reduction route for synthesis of an ER processing α-glucosidase I substrate
  作者：Kenta Iino、Shogo Iwamoto、Yuta Kasahara、Kana Matsuda、Takashi Tonozuka、Atsushi Nishikawa、Yukishige Ito、Ichiro Matsuo

  DOI：10.1016/j.tetlet.2012.06.061

  日期：2012.8

  The fluorescence-labeled hexasaccharide (Glc alpha 1-2Glc alpha 1-3Glc alpha 1-3Man alpha 1-2Man alpha 1-2Man alpha) was synthesized as a substrate for the processing enzyme alpha-glucosidase I. To construct the 1,2-cis glucosidic linkages, we employed an alpha stereoselective coupling using the mannosyl donor by assisted neighboring-group participation, followed by conversion of the stereochemistry of the C-2 hydroxyl group in the mannose residue using sequential oxidation of C-2 hydroxyl group to a 2-keto group and stereoselective reduction of the hydroxyl group to the gluco-configuration to provide the corresponding alpha-glucoside derivative. Using this strategy, the three consecutive alpha-glucosidic linkages were easily obtained in a stereoselective manner. Finally, the Dansyl labeled hexasaccharide derivative was used to measure the activity of processing alpha-glucosidase I. (c) 2012 Elsevier Ltd. All rights reserved.
• CHERNYAK, A. YA.;ANTONOV, K. V.;KOCHETKOV, N. K., BIOORGAN. XIMIYA, 15,(1989) N, S. 1113-1127
  作者：CHERNYAK, A. YA.、ANTONOV, K. V.、KOCHETKOV, N. K.

  DOI：——

  日期：——