4-methylphenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside | 1407967-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside
• 英文别名: (4-methylphenyl) 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside
• CAS: 1407967-81-0
• 化学式: C₃₈H₃₆O₅S
• 分子量: 604.767
• InChiKey: JFRBWRXJWVNOIL-DTGQXANJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.25
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside 在 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以76%的产率得到p-tolyl 2,4-di-O-benzyl-3-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  General Homologation Strategy for Synthesis of l-glycero- and d-glycero-Heptopyranoses

  摘要：

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

  DOI：

  10.1021/acs.orglett.5b02620
• 作为产物：
  描述：

  溴甲苯 、 2-溴甲基萘 、 4-甲基苯基 4,6-O-亚苄基-1-硫代-α-D-吡喃甘露糖苷 在 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲苯 、 水 为溶剂， 反应 6.0h， 以91%的产率得到4-methylphenyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside
  参考文献：
  名称：

  N ？O键作为糖苷键替代物：多羟基N-烷氧基哌啶的合成研究

  摘要：

  通过将高度官能化的1,5-二醛与各种羟胺进行双环双还原胺化（DRA），合成了一系列新型的多羟基N-烷氧基哌啶。所需的基于糖的二醛是由环戊二烯化钠分七步高效制备的。已经为DRA开发了两步协议。脱保护后，它导致了异黄酮，3-脱氧异氟谷氨酸和许多其他N-烷氧基类似物。通过变温NMR方法发现这些多羟基化的N-烷氧基哌啶衍生物的转化障碍约为15 kcal mol -1。除了N-hydroxyisofagomine本身，所制备的化合物均未显示出对甜杏仁β-葡萄糖苷酶的显着抑制活性。

  DOI：

  10.1002/chem.201202374

文献信息

• 2-(Selenocyanatomethyl)-2-propenol — A convenient synthon for ligation via the deselenative allylic rearrangement of allyl selenosulfides: preparation, functional group compatibility, and application
  作者：David Lachkar、Caroline Boudet、Xavier Guinchard、David Crich

  DOI：10.1139/v2012-056

  日期：2012.11

  The preparation and reactions of 2-(selenocyanatomethyl)-2-propenol are described and reveal the compatibility of the allylic selenocyanate group with a range of mild oxidizing and Lewis acidic conditions. 2-(Selenocyanatomethyl)-2-propenol and its derivatives are employed in the functionalization of simple and amino acid derived thiols in methanolic solution at room temperature to give 2-(hydroxymethyl)allyl

  描述了 2-(硒氰酸根合甲基)-2-丙烯醇的制备和反应，并揭示了烯丙基硒氰酸酯基团与一系列温和氧化和路易斯酸性条件的相容性。2-(硒氰基甲基)-2-丙烯醇及其衍生物用于室温下甲醇溶液中简单和氨基酸衍生的硫醇的官能化，以良好至极好的收率得到2-(羟甲基)烯丙基硫化物。
• Synthetic Neoglycoconjugates of Hepta‐ and Nonamannoside Ligands for Eliciting Oligomannose‐Specific HIV‐1‐Neutralizing Antibodies
  作者：Matteo Cattin、Jean‐François Bruxelle、Kurtis Ng、Markus Blaukopf、Ralph Pantophlet、Paul Kosma

  DOI：10.1002/cbic.202200061

  日期：2022.4.5

  AbstractOligomannose‐type glycans on the spike protein of HIV‐1 constitute relevant epitopes to elicit broadly neutralizing antibodies (bnAbs). Herein we describe an improved synthesis of α‐ and β‐linked hepta‐ and nonamannosyl ligands that were subsequently converted into BSA and CRM197 neoglycoconjugates. We assembled the ligands from anomeric 3‐azidopropyl spacer glycosides from select 3‐O‐protected thiocresyl mannoside donors. Chain extensions were achieved using [4+3] or [4+5] block synthesis of thiocresyl and trichloroacetimidate glycosyl donors. Subsequent global deprotection generated the 3‐aminopropyl oligosaccharide ligands. ELISA binding data obtained with the β‐anomeric hepta‐ and nonamannosyl conjugates with a selection of HIV‐1 bnAbs showed comparable binding of both mannosyl ligands by Fab fragments yet lesser binding of the nonasaccharide conjugate by the corresponding IgG antibodies. These results support previous observations that a complete Man9 structure might not be the preferred antigenic binding motif for some oligomannose‐specific antibodies, and have implications for glycoside designs to elicit oligomannose‐targeted HIV‐1‐neutralizing antibodies.