4,5-dihydrothiazol-2-yl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside | 810670-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-dihydrothiazol-2-yl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: 2-thiazolinyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-6-(4,5-dihydro-1,3-thiazol-2-ylsulfanyl)-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 810670-84-9
• 化学式: C₃₀H₂₇NO₈S₂
• 分子量: 593.678
• InChiKey: PBZVRYKEQDCNFD-YVXTWPRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  41
• 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：
  171
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 、 4,5-dihydrothiazol-2-yl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 3 A molecular sieve 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以45%的产率得到4,5-dihydrothiazol-2-yl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  S-噻唑啉基（STaz）糖苷是用于聚合选择性，化学选择性和正交寡糖合成的通用构建基块。

  摘要：

  为了开发有效寡糖组装的新方法，已合成了一系列S-噻唑啉基（STaz）糖苷。这些新颖的衍生物针对各种反应条件进行了评估，并显示出能够以武装-解除武装的方式进行化学选择性活化。此外，与其他常见的离去基团相比，S-噻唑啉基部分显示出显着的选择性活化倾向。相反，可以在STaz部分上选择性激活各种离去基团，从而允许STaz / S-乙基和STaz / S-苯基正交方法。为了证明新型STaz衍生物的多功能性，已经以收敛的选择性，正交和化学选择性方式合成了许多寡糖靶标。

  DOI：

  10.1002/chem.200600262
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以4.20 g的产率得到4,5-dihydrothiazol-2-yl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  通过暂时失活的S-噻唑基糖苷作为糖基受体合成寡糖的新策略。

  摘要：

  已经开发出一种新的糖基化策略，其允许在具有相同异头基团的暂时失活的糖基受体上化学选择性活化糖基供体的S-噻唑基（STaz）部分。通过使糖基受体的STaz部分结合到稳定的钯（II）络合物中来实现这种失活。因此，然后通过简单的配体交换从复合物中释放获得的二糖。[反应：看文字]

  DOI：

  10.1021/ol048043y

文献信息

• Application of Glycosyl Thioimidates in Solid-Phase Oligosaccharide Synthesis
  作者：M. Cristina Parlato、Medha N. Kamat、Haisheng Wang、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1021/jo701902f

  日期：2008.3.1

  S-benzoxazolyl (SBox) and S-thiazolinyl (STaz) glycosides, were investigated as glycosyl donors for solid-phase oligosaccharide synthesis. It was demonstrated that these derivatives are suitable for both glycosyl acceptor-bound and glycosyl donor-bound strategies, commonly employed in resin-supported oligosaccharide synthesis.

  研究了两类稳定的硫代酰亚胺基衍生物，即S-苯并恶唑基（SBox）和S-噻唑啉基（STaz）糖苷，作为固相寡糖合成的糖基供体。已证明这些衍生物既适用于糖基受体结合的策略，也适用于糖基供体结合的策略，通常用于树脂支持的寡糖合成中。
• Synthesis, characterization and reactivity of carbohydrate platinum(iv) complexes with thioglycoside ligands
  作者：Cornelia Vetter、Papapida Pornsuriyasak、Jürgen Schmidt、Nigam P. Rath、Tobias Rüffer、Alexei V. Demchenko、Dirk Steinborn

  DOI：10.1039/b927058b

  日期：——

  fac-[PtMe3(4,4′-R2bpy)(Me2CO)][BF4] (R = H, 1a; tBu, 1b) and fac-[PtMe3(OAc-κ2O,O′)(Me2CO)] (2), respectively, with thioglycosides containing thioethyl (ch-SEt) and thioimidate (ch-STaz, Taz = thiazoline-2-yl) anomeric groups led to the formation of the carbohydrate platinum(IV) complexes fac-[PtMe3(4,4′-R2bpy)(ch*)][BF4] (ch* = ch-SEt, 8–14; ch-STaz, 15–23) and fac-[PtMe3(OAc-κ2O,O′)(ch*)] (ch* = ch-SEt, 24–28;

  的反应FAC - [PTME 3（4,4'-R 2联吡啶）（ME 2 CO）] [BF 4 ]（R =H, 1a ;Ť卜, 1b ) 和fac -[PtMe 3 (OAc-κ 2 O , O ')(Me 2 CO)]( 2 )、分别含硫糖苷硫乙基 (ch-SEt） 和 硫代亚氨酸盐 (ch-STAz, 塔兹 = 噻唑啉-2-基) 异头基团导致碳水化合物铂 ( IV ) 复合物fac -[PtMe 3 (4,4'-R 2 bpy)(ch*)][BF 4 ] (ch* = ch-SEt, 8–14 ; ch-STAz, 15–23 ) 和fac -[PtMe 3 (OAc-κ 2 O , O ')(ch*)](ch* = ch-SEt, 24–28 ; ch-STaz = 29–35 )，分别。核磁共振 ( 1 H,13 ℃, 195铂) 光谱研究和19 (ch-STaz =2-噻唑啉基 2,3
• A Novel Strategy for Oligosaccharide Synthesis via Temporarily Deactivated <i>S</i>-Thiazolyl Glycosides as Glycosyl Acceptors
  作者：Papapida Pornsuriyasak、Umesh B. Gangadharmath、Nigam P. Rath、Alexei V. Demchenko

  DOI：10.1021/ol048043y

  日期：2004.11.1

  activation of the S-thiazolyl (STaz) moiety of a glycosyl donor over the temporarily deactivated glycosyl acceptor, bearing the same anomeric group, has been developed. This deactivation is achieved by engaging of the STaz moiety of the glycosyl acceptor into a stable palladium(II) complex. Therefore, obtained disaccharides are then released from the complex by simple ligand exchange. [reaction: see text]

  已经开发出一种新的糖基化策略，其允许在具有相同异头基团的暂时失活的糖基受体上化学选择性活化糖基供体的S-噻唑基（STaz）部分。通过使糖基受体的STaz部分结合到稳定的钯（II）络合物中来实现这种失活。因此，然后通过简单的配体交换从复合物中释放获得的二糖。[反应：看文字]
• Development of an Arming Participating Group for Stereoselective Glycosylation and Chemoselective Oligosaccharide Synthesis
  作者：James T. Smoot、Papapida Pornsuriyasak、Alexei V. Demchenko

  DOI：10.1002/anie.200502694

  日期：2005.11.4
• How the Arming Participating Moieties can Broaden the Scope of Chemoselective Oligosaccharide Synthesis by Allowing the Inverse Armed−Disarmed Approach
  作者：James T. Smoot、Alexei V. Demchenko

  DOI：10.1021/jo801551r

  日期：2008.11.21

  A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety, a novel neighboring group that is capable of efficient participation via a six-membered intermediate. The application of the picolyl concept to glycosidations of thioimidoyl, thioglycosyl, and trichloroacetimidoyl glycosyl donors is demonstrated. The picolyl moiety also retains the glycosyl donor in the armed state, as opposed to conventional acyl participating moieties. We name this new approach the "inverse armed-disarmed" strategy, because it allows for the chemoselective introduction of a 1,2-trans glycosidic linkage prior to other linkages. In the context of the oligosaccharide synthesis, the strategy provides trans-trans and trans-cis patterned oligosaccharides as opposed to classic Fraser-Reid's armed-disarmed approach leading to cis-trans and cis-cis linkages.