methyl 3-O-(p-methoxybenzyl)-β-L-rhamnopyranoside | 676127-51-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-(p-methoxybenzyl)-β-L-rhamnopyranoside
• 英文别名: (2S,3R,4R,5S,6S)-2-methoxy-4-[(4-methoxyphenyl)methoxy]-6-methyloxane-3,5-diol
• CAS: 676127-51-8
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: ATMZRMFKCSTXSL-NBUQLFNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-O-(p-methoxybenzyl)-β-L-rhamnopyranoside 在 吡啶 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 生成 methyl 2,4-di-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018
• 作为产物：
  描述：

  L-rhamnose hydrate 在 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 methyl 3-O-(p-methoxybenzyl)-β-L-rhamnopyranoside
  参考文献：
  名称：

  2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products

  摘要：

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.018

文献信息

• β-Selective xylulofuranosylation <i>via</i> a conformationally-restricted glycosyl donor
  作者：Bo-Shun Huang、Todd L. Lowary

  DOI：10.1039/d0ob00260g

  日期：——

  Reported is the first stereoselective method for β-xylulofuranosylation, which employs 3,4-O-xylylene-protected thioglycoside donors.

  报道了第一种β-木糖呋喃糖基选择性方法，该方法使用3,4-O-二甲苯基保护的硫代糖苷供体。
• 2,4-Diazido-2,4,6-trideoxy-l-hexopyranoses as valuable building units in the synthesis of natural products
  作者：Anna Banaszek、Vladimir Zaitsev

  DOI：10.1016/j.tetasy.2003.11.018

  日期：2004.1

  Synthesis of five L-enantiomers of 2,4-diazido-2,4,6-trideoxy-pyranoses has been accomplished. These sugars were prepared via the regioselective protection of hydroxyl groups in L-rhamnoside and L-fucoside, followed by triflation and subsequent S(N)2 substitution with azido nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.