phenyl 2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside | 179072-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-4-ol
• CAS: 179072-65-2
• 化学式: C₃₃H₃₄O₅S
• 分子量: 542.696
• InChiKey: NXYJIFNUJVTKJX-CYEGLCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,4,6-tri-O-benzyl-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， 以 二氯甲烷 为溶剂， 反应 1.0h， 以38%的产率得到2,4,6-tri-O-benzyl-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 2,4,6-tri-O-benzyl-3-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.67h， 以87%的产率得到phenyl 2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Orthogonal glycosylation strategy in synthesis of extended blood group B determinant

  摘要：

  The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00901-x

文献信息

• Solid-Phase Synthesis of Oligosaccharides and On-Resin Quantitative Monitoring Using Gated Decoupling ¹³C NMR
  作者：Takuya Kanemitsu、Chi-Huey Wong、Osamu Kanie

  DOI：10.1021/ja0167396

  日期：2002.4.1

  A general strategy for solid-phase oligosaccharide synthesis capable of nondestructive quantitative monitoring has been developed. The synthesis was carried out on TentaGel using thioglycosides as glycosylating agents and dimethylthiomethylsulfonium triflate as the activator. An acylsulfonamide linker was introduced to cleave the oligosaccharide from the resin. The solid-phase reactions were monitored

  已经开发出能够进行无损定量监测的固相寡糖合成的一般策略。合成是在 TentaGel 上进行的，使用硫糖苷作为糖基化剂，使用二甲基硫代甲基锍三氟甲磺酸盐作为活化剂。引入酰基磺酰胺接头以从树脂上裂解寡糖。通过使用 13C NMR 的反向门控去耦技术对固相反应进行定量监测，其中使用两种富含 13C 的标记物来监测反应：一种是作为接头的一部分并作为内标的富含 13C 的甘氨酸，另一个是富含 13C 的乙酰基，用作糖基化试剂的保护基团。展示了唾液酸路易斯 X 支链四糖的代表性合成。
• Synthesis of 1,1-Linked Galactosyl Mannosides Carrying a Thiazine Ring as Mimetics of Sialyl Lewis X Antigen:  Investigation of the Effect of Carboxyl Group Orientation on P−Selectin Inhibition
  作者：Kayoko Shibata、Kazumi Hiruma、Osamu Kanie、Chi-Huey Wong

  DOI：10.1021/jo991556b

  日期：2000.4.1

  mannosides as sialyl Lewis X mimetics that contain a spiro-ring to position the carboxylate group in a well-defined orientation. It was found that compound 4 is more active as a P-selectin inhibitor (IC50 = 19 microM) than the parent disaccharide 2, which contains a flexible carboxyl group (IC50 = 193 microM). This result is consistent with that observed in the previous NMR study of sialyl Lewis X bound to

  本文描述了1,1-连接的半乳​​糖基甘露糖苷的合成方法，即唾液酸化的Lewis X模拟物，其中包含一个螺环，可将羧酸酯基团定位在明确的方向上。发现化合物4作为P-选择蛋白抑制剂（IC 50 ＝19μM）比具有柔性羧基的母体二糖2（IC 50 ＝193μM）更具活性。该结果与先前的对P-选择蛋白结合的唾液酸路易斯X的NMR研究中观察到的结果一致。此处描述的化学方法对于开发E-，P-和L-选择蛋白的选择性抑制剂应该是有用的。
• 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。
• Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations
  作者：Ju Yuel Baek、Hea-Won Kwon、Se Jin Myung、Jung Jun Park、Mi Young Kim、Dominea C.K. Rathwell、Heung Bae Jeon、Peter H. Seeberger、Kwan Soo Kim

  DOI：10.1016/j.tet.2015.06.014

  日期：2015.8

  Glucosylations and galactosylations of various acceptors with donors possessing an electronwithdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A beta-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an alpha-directing effect. The alpha-directing effect is partly considered to remote participation of the acyl groups, whereas the beta-directing effect is somewhat attributed to the S(N)2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the alpha-glycosyl triflates was determined by a low-temperature NMR study. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.