phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 700363-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-[(2R,3S,4R,5R,6S)-4-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• CAS: 700363-88-8
• 化学式: C₄₉H₄₆N₂O₁₆S
• 分子量: 950.974
• InChiKey: OCMYKDPHMTXNQZ-LSKGBVNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  68
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  242
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 三氯异氰尿酸 、 水 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以86%的产率得到3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranose
  参考文献：
  名称：

  Trichloroisocyanuric acid (TCCA): an efficient green reagent for activation of thioglycosides toward hydrolysis

  摘要：

  Trichloroisocyanuric acid (TCCA), an inexpensive, commercially available, and non-toxic reagent has been used for the activation of thioglycosides toward their hydrolysis to the corresponding hemiacetals in high to excellent yields. The methodology provides a mild reaction condition for dealing with compounds containing acid sensitive functional groups. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.01.001
• 作为产物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 1-(苯基亚硫酰基)哌啶 、 2,6-di-tert-butyl-4-methyl piperidine 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  2-脱氧-2-氨基硫代糖苷的迭代糖基化及其在线性低聚葡糖胺的组合合成中的应用。

  摘要：

  DOI：

  10.1002/anie.200353552

文献信息

• Convergent synthesis of the tetrasaccharide repeating unit related to the O-antigenic polysaccharide of Escherichia coli 78
  作者：Sajal K. Maity、Amarendra Patra、Rina Ghosh

  DOI：10.1016/j.tet.2010.02.052

  日期：2010.4

  A convergent synthesis of the tetrasaccharide repeating unit of the O-antigenic cell wall polysaccharide of Escherichia coli 78, as the corresponding methyl glycoside (I), is being reported. It involved stereoselective glycosidation of a beta-linked mannodisaccharide acceptor with a beta-linked glucosamine based disaccharide thioglycoside donor, which were prepared from the corresponding functionalised monosaccharide based glycosyl donors and acceptors. The resulting tetrasaccharide derivative was finally converted to (I) by selective deprotection and also by global protection and deprotection techniques. (C) 2010 Elsevier Ltd. All rights reserved.