phenyl 3,4,6-tri-O-benzyl-2-O-chloroacetyl-1-thio-β-D-galactopyranoside | 819798-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-benzyl-2-O-chloroacetyl-1-thio-β-D-galactopyranoside
• 英文别名: phenyl-2-O-chloroacetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside；ClAc(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(b)-SPh；[(2S,3R,4S,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] 2-chloroacetate
• CAS: 819798-05-5
• 化学式: C₃₅H₃₅ClO₆S
• 分子量: 619.178
• InChiKey: OVTHQCDFBAMHMT-DNNCLPCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-benzyl-2-O-chloroacetyl-1-thio-β-D-galactopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 二乙胺基三氟化硫 作用下， 反应 1.0h， 以68%的产率得到3,4,6-tri-O-benzyl-2-O-chloroacetyl-α-D-galactopyranosyl fluoride
  参考文献：
  名称：

  METHOD OF SYNTHESIZING SUGAR CHAIN

  摘要：

  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。

  公开号：

  EP1640379A1
• 作为产物：
  描述：

  phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 吡啶 、 硼烷四氢呋喃络合物 、 三氟甲磺酸 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 phenyl 3,4,6-tri-O-benzyl-2-O-chloroacetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  肺炎链球菌和口腔链球菌Uo5脂蛋白酸的脂质-锚固核心三糖的全合成。

  摘要：

  在本文中，我们报告了肺炎链球菌和口腔链球菌Uo5的脂锚附体脂锚酸的核心三糖的有效全合成。关键特征包括通过一锅顺序SN2反应方便地合成稀有糖2,4,6-苯三氧基-2-乙酰氨基-4-氨基-d-Galp结构单元以及d-硫代葡萄糖苷与α-选择性偶联的α-选择性偶联二酰基甘油受体来构建通用的二糖受体，该二糖受体可用于目标分子1和2的全合成。

  DOI：

  10.1021/acs.orglett.9b04264

文献信息

• An improved method for the synthesis of protected glycosyl fluorides from thioglycosides using N,N-diethylaminosulfur trifluoride (DAST)
  作者：Katsuhiko Suzuki、Yukishige Ito、Osamu Kanie

  DOI：10.1016/j.carres.2012.07.003

  日期：2012.10

  examined using N,N-diethylaminosulfur trifluoride (DAST). Although the reaction proceeded without N-bromosuccinimide (NBS), in some cases it was found that the electrophilicity of the Vilsmeier-type electrophilic sulfinium cation species was not sufficient for the activation of certain less-reactive thioglycosides. Here, we report the results of fluorination reactions of a series of monosaccharides using

  使用N，N-二乙基氨基三氟化硫（DAST）检查了硫糖苷直接转化为寡糖合成中常用的糖基氟化物。尽管反应在没有N-溴代琥珀酰亚胺（NBS）的情况下进行，但在某些情况下，发现Vilsmeier型亲电electro阳离子物种的亲电性不足以活化某些反应性较低的硫代糖苷。在这里，我们报告了在不存在NBS的情况下使用DAST进行的一系列单糖氟化反应的结果，并讨论了在存在二甲基（甲硫基）s三氟甲烷磺酸盐（DMTST）的情况下加速反应的过程，从而提高了产品收率。
• Method for synthesizing sugar chain(s)
  申请人：Kanie Osamu

  公开号：US20060166278A1

  公开（公告）日：2006-07-27

  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高效地化学合成生物分子的方法，包括核苷酸（核酸）、肽（蛋白质）或糖链等代表性分子。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，该反应系统包含多种单糖单元，其特征在于根据反应系统中副反应的减少作为指标确定的温度升高速率来改变糖链合成反应系统中的温度。
• Synthesis of a library of fucopyranosyl-galactopyranosides consisting of a complete set of anomeric configurations and linkage positions
  作者：Isao Ohtsuka、Takuro Ako、Rumiko Kato、Shusaku Daikoku、Satomi Koroghi、Takuya Kanemitsu、Osamu Kanie

  DOI：10.1016/j.carres.2006.03.040

  日期：2006.7

  A library composed of a complete set of fucopyranosyl-galactopyranosides was synthesized. A perbenzylated phenylthio fucopyranoside and a series of tri-O-benzyl-galactopyranosyl fluorides having single hydroxyl groups at the 2-, 3-, 4-, and 6-positions were used as the glycosyl donor and glycosyl acceptors, respectively. The chosen set of functionalities at the anomeric centers enabled rapid access to the oligosaccharides based on chemoselective activation. The first coupling reaction was achieved by the action of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST). The resulting disaccharide fluoride was readily activated by hafnocene bistrifluoromethanesulfonate [Cp2Hf(OTf)(2)] and glycosidated with n-octanol. (c) 2006 Elsevier Ltd. All rights reserved.
• 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。
• Total Synthesis of the Lipid-Anchor-Attached Core Trisaccharides of Lipoteichoic Acids of <i>Streptococcus pneumoniae</i> and <i>Streptococcus oralis</i> Uo5
  作者：Balasaheb K. Ghotekar、Ananda Rao Podilapu、Suvarn S. Kulkarni

  DOI：10.1021/acs.orglett.9b04264

  日期：2020.1.17

  Herein we report an efficient total synthesis of lipid-anchor-appended core trisaccharides of lipoteichoic acids of Streptococcus pneumoniae and Streptococcus oralis Uo5. The key features include the expedient synthesis of the rare sugar 2,4,6-trideoxy-2-acetamido-4-amino-d-Galp building block via one-pot sequential SN2 reactions and the α-selective coupling of d-thioglucoside with the diacyl glycerol

  在本文中，我们报告了肺炎链球菌和口腔链球菌Uo5的脂锚附体脂锚酸的核心三糖的有效全合成。关键特征包括通过一锅顺序SN2反应方便地合成稀有糖2,4,6-苯三氧基-2-乙酰氨基-4-氨基-d-Galp结构单元以及d-硫代葡萄糖苷与α-选择性偶联的α-选择性偶联二酰基甘油受体来构建通用的二糖受体，该二糖受体可用于目标分子1和2的全合成。