phenyl 2,3,6-tri-O-benzyl-4-O-(3-carboxypropanoyl)-1-thio-α-D-mannopyranoside | 316188-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,6-tri-O-benzyl-4-O-(3-carboxypropanoyl)-1-thio-α-D-mannopyranoside
• 英文别名: 2,3,6-tri-O-benzyl-4-O-succinoyl-1-thio-β-D-mannopyranoside；4-[(2R,3R,4S,5S,6R)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-4-oxobutanoic acid
• CAS: 316188-25-7
• 化学式: C₃₇H₃₈O₈S
• 分子量: 642.77
• InChiKey: XTXXWKBIDACGPK-FCLJRDIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,6-tri-O-benzyl-4-O-(3-carboxypropanoyl)-1-thio-α-D-mannopyranoside 在 盐酸 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 3 Angstroem MS 、 sodium methylate 、 sodium cyanoborohydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 48.0h， 生成
  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：

  2,3-双-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代- a-D--吡喃甘露糖苷苯酯 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 3 Angstroem MS 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 生成 phenyl 2,3,6-tri-O-benzyl-4-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

文献信息

• METHOD OF SYNTHESIZING SUGAR CHAIN
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1640379A1

  公开（公告）日：2006-03-29

  An object of the present invention is to provide a method for efficiently chemically synthesizing biomolecules including a nucleotide (nucleic acid), a peptide (protein), or a sugar chain, as representative examples. The present invention provides a method of solid-phase synthesis of sugar chain(s) for synthesizing multiple types of sugar chains in at least one sugar chain synthesis reaction system comprising multiple types of monosaccharide units, which is characterized in that it comprises changing the temperature in the sugar chain synthesis reaction system depending on the temperature rising rate that has been determined based on a decrease in side reaction(s) in the reaction system as an indicator.

  本发明的目的是提供一种有效地化学合成生物分子的方法，包括核苷酸（核酸）、肽（蛋白质）或糖链等代表性示例。本发明提供了一种固相合成糖链的方法，用于在至少一个糖链合成反应系统中合成多种类型的糖链，其特征在于根据已确定的反应系统中副反应减少的指标，改变糖链合成反应系统中的温度上升速率。
• ——
  作者：Gregor Lemanski、Thomas Ziegler

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

  日期：2000.10.4

  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.