p-methylphenyl 2,3-di-O-(p-methylbenzoyl)-1-thio-β-D-glucopyranoside | 443958-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2,3-di-O-(p-methylbenzoyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-5-(4-methylbenzoyl)oxy-6-(4-methylphenyl)sulfanyloxan-4-yl] 4-methylbenzoate
• CAS: 443958-79-0
• 化学式: C₂₉H₃₀O₇S
• 分子量: 522.619
• InChiKey: STHWLMIQBJRFQS-KPTFLJRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2,3-di-O-(p-methylbenzoyl)-1-thio-β-D-glucopyranoside 在 水 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以87%的产率得到[(2R,3R,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-5-(4-methylbenzoyl)oxy-6-(4-methylphenyl)sulfinyloxan-4-yl] 4-methylbenzoate
  参考文献：
  名称：

  Selective Oxidation of Glycosyl Sulfides to Sulfoxides Using Magnesium Monoperoxyphthalate and Microwave Irradiation

  摘要：

  A protocol that uses moist magnesium monoperoxyphthalate (MMPP) as an oxidant under microwave irradiation rapidly yields a variety of glycosyl sulfoxides from corresponding sulfides in high yields with high selectivity.

  DOI：

  10.1021/jo035698o
• 作为产物：
  描述：

  在 四溴化碳 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以88%的产率得到p-methylphenyl 2,3-di-O-(p-methylbenzoyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions

  摘要：

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.095

文献信息

• An efficient and selective method for preparing glycosyl sulfoxides by oxidizing glycosyl sulfides with OXONE or t-BuOOH on SiO2
  作者：Ming-Yi Chen、Laxmikant Narhari Patkar、Hui-Ting Chen、Chun-Cheng Lin

  DOI：10.1016/s0008-6215(03)00164-2

  日期：2003.6

  Silica gel adsorbed with OXONE or t-BuOOH was used as a mild oxidant to selectively oxidize glycosyl sulfides to corresponding sulfoxides in good yields and without sulfones formation. This method was also found compatible with various other functional groups in the glycosides. (C) 2003 Elsevier Science Ltd. All rights reserved.