phenyl 3-O-allyl-1-thio-β-D-glucopyranoside | 197005-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-allyl-1-thio-β-D-glucopyranoside
• 英文别名: Phenyl 3-O-2-propen-1-yl-1-thio-I(2)-D-glucopyranoside；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-phenylsulfanyl-4-prop-2-enoxyoxane-3,5-diol
• CAS: 197005-23-5
• 化学式: C₁₅H₂₀O₅S
• 分子量: 312.387
• InChiKey: SKCRVDVCBSFAGE-ZSAUSMIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-allyl-1-thio-β-D-glucopyranoside 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.5h， 生成 phenyl 3-O-allyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  d‐Glucose as a Regioselectively Addressable Scaffold for Combinatorial Chemistry on Solid Phase

  摘要：

  D-Glucose derivatives bearing an anomeric thiophenyl group and orthogonally protections on secondary hydroxyl groups were linked to solid supports (PS/DV polymer, tentagel resin) through an ester bond on C-6. It was investigated the possibility to remove orthogonally protecting groups and functionalize selectively the free hydroxyls groups and the anomeric carbon of sugars in solid phase.

  DOI：

  10.1081/car-120019014
• 作为产物：
  描述：

  1,2,4,6-四-O-乙酰基-3-O-烯丙基-β-D-吡喃葡萄糖 在 三氟化硼乙醚 、 sodium 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 phenyl 3-O-allyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  d‐Glucose as a Regioselectively Addressable Scaffold for Combinatorial Chemistry on Solid Phase

  摘要：

  D-Glucose derivatives bearing an anomeric thiophenyl group and orthogonally protections on secondary hydroxyl groups were linked to solid supports (PS/DV polymer, tentagel resin) through an ester bond on C-6. It was investigated the possibility to remove orthogonally protecting groups and functionalize selectively the free hydroxyls groups and the anomeric carbon of sugars in solid phase.

  DOI：

  10.1081/car-120019014

文献信息

• Copper(II) Triflate: A Versatile Catalyst for the One-Pot Preparation of Orthogonally Protected Glycosides
  作者：Anh-Tuan Tran、Rachel A. Jones、Julien Pastor、Julien Boisson、Nichola Smith、M. Carmen Galan

  DOI：10.1002/adsc.201100228

  日期：2011.10

  development of general and expedient methodologies for the preparation of orthogonally protected glycoside building blocks is essential for the efficient synthesis of complex oligosaccharides. Herein, we describe a new approach that uses copper(II) triflate as a versatile catalyst for the one-pot preparation of orthogonal protected thio- and O-glycosides from the corresponding unprotected counterparts. The conditions

  制备正交保护的糖苷结构单元的通用方法和便捷方法对于有效合成复杂寡糖至关重要。在这里，我们描述了一种新的方法，该方法使用三氟甲磺酸铜（II）作为通用催化剂，从相应的未保护对应物一锅制备正交保护的硫代和O型糖苷。条件温和，易于处理，适用于两个和三个一锅串联转化，包括亚芳基乙缩醛化，酯化，区域选择性还原性乙缩醛开环，糖基化和甲硅烷基化过程。
• <scp>d</scp>‐Glucose as a Regioselectively Addressable Scaffold for Combinatorial Chemistry on Solid Phase
  作者：Francesco Peri、Francesco Nicotra、Colin P. Leslie、Fabrizio Micheli、Pierfausto Seneci、Carla Marchioro

  DOI：10.1081/car-120019014

  日期：2003.1.3

  D-Glucose derivatives bearing an anomeric thiophenyl group and orthogonally protections on secondary hydroxyl groups were linked to solid supports (PS/DV polymer, tentagel resin) through an ester bond on C-6. It was investigated the possibility to remove orthogonally protecting groups and functionalize selectively the free hydroxyls groups and the anomeric carbon of sugars in solid phase.