phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside | 201056-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aS)-8-hydroxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] acetate
• CAS: 201056-61-3
• 化学式: C₂₁H₂₂O₆S
• 分子量: 402.468
• InChiKey: GWTONIWBPILHGT-RLLAOZKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 一水合肼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 phenyl 3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Trisaccharide of Incanoside from Caryopteris incana

  摘要：

  Trisaccharide phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl-(1 --> 2)-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3 --> 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside, the sugar core of incanosides from Caryopteris incana (T-HUNB.), was synthesized via a concise route. The key step of this route involved the preparation of decisive disaccharide acceptor from the phenyl 2-acetyl-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-2-O-acetyl-4,6-O-benzylidene-1-thio-beta-D-glucopyranoside by regioselective and chemoselective deacetylation method.

  DOI：

  10.1081/scc-120027292
• 作为产物：
  描述：

  1-硫代-b-D-吡喃葡萄糖苷对甲苯酯 在 pseudomonas fluorescens lipase 、 D(+)-10-樟脑磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 45.0~50.0 ℃ 、2.67 kPa 条件下， 反应 42.0h， 生成 phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  区域选择性脂肪酶催化的4,6 - O-亚苄基-α-和-β-d-吡喃糖苷衍生物的酰化反应，显示出一系列的端基取代基

  摘要：

  脂肪酶的到应用的效果的区域选择性C-3- Ö的酰化-和-galactopyranosides显示范围的端基异构体的取代基，和C-2- Ö苯基的酰化和乙基报道。特别地，该方法允许在乙基11的C-3羟基处引入各种酰基保护基。

  DOI：

  10.1016/s0040-4020(98)00935-1

文献信息

• Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides
  作者：Sibin Wang、Oleksii Zhelavskyi、Jeonghyo Lee、Alonso J. Argüelles、Yaroslav Ya. Khomutnyk、Enoch Mensah、Hao Guo、Rami Hourani、Paul M. Zimmerman、Pavel Nagorny

  DOI：10.1021/jacs.1c08448

  日期：2021.11.10

  differentially protected mono- and disaccharide derivatives. To further demonstrate the utility of the polymeric catalysts, the same batch of (R)-Ad-TRIP-PS catalyst was recycled and reused to accomplish single-pot gram-scale syntheses of 6 differentially protected d-glucose derivatives. The subsequent exploration of the reaction mechanism using NMR studies of deuterated and nondeuterated substrates revealed

  本文介绍了使用手性磷酸 (CPA) 及其固定化聚合物变体 ( R )-Ad-TRIP-PS 和 ( S )-SPINOL-PS 作为催化剂对单糖二醇进行区域选择性缩醛保护的研究。这些催化剂控制的区域选择性缩醛化反应对各种d-葡萄糖-、 d-半乳糖-、 d-甘露糖-和l-岩藻糖衍生的 1,2-二醇具有高区域选择性（高达 >25:1 rr）并且可以根据手性催化剂的选择以区域发散的方式进行。聚合物催化剂可以方便地回收并多次重复使用，用于克级官能化，催化负载量低至 0.1 mol%，并且它们的性能通常优于其单体变体的性能。这些区域选择性 CPA 催化的缩醛化与常见的羟基官能化成功地结合为单锅套叠程序，产生了 32 种区域异构纯的差异保护的单糖和二糖衍生物。为了进一步证明聚合物催化剂的实用性，同一批的( R )-Ad-TRIP-PS催化剂被回收并重复使用，以完成6种差异保护的d-葡萄糖衍生物的单锅克
• Gridley, Jonathan J.; Hacking, Andrew J.; Osborn, Helen M. I., Synlett, 1997, # 12, p. 1397 - 1399
  作者：Gridley, Jonathan J.、Hacking, Andrew J.、Osborn, Helen M. I.、Spackman, David G.

  DOI：——

  日期：——
• An Efficient and Regioselective Deprotection Method for Acetylated Glycosides
  作者：Jubiao Li、Yanguang Wang

  DOI：10.1081/scc-120027255

  日期：2004.1

  A new regioselective 2-O-deacetylation methodology of acetylated glycosides using 85% hydrazine hydrate in THF is described. Using this method, acetylated 1-thio-glycoside could also be selectively deprotected to give 3-O-deprotected compound.
• Synthesis of Vancomycin from the Aglycon
  作者：Christopher Thompson、Min Ge、Daniel Kahne

  DOI：10.1021/ja983504u

  日期：1999.2.1

  Vancomycin-resistant bacterial strains pose a serious threat to human health. Efforts to overcome vancomycin resistance by modifying the natural product have shown that the carbohydrates help modulate biological activity. To explore the mechanisms by which the carbohydrates function, it would be useful to have access to vancomycin derivatives containing different disaccharides. We now describe the synthesis of vancomycin from a readily available protected aglycon. This chemistry lays the groundwork for wide-ranging investigations of the roles of the carbohydrates in the biological activity of vancomycin. Moreover, in developing methods to glycosylate vancomcyin, we have extended the utility of the sulfoxide glycosylation reaction considerably by making it possible to use unhindered esters as neighboring groups. The chemistry we describe may also have implications for how to improve some other glycosylation methods.