isopropyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside | 946499-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside
• CAS: 946499-63-4
• 化学式: C₁₅H₂₄O₇S
• 分子量: 348.417
• InChiKey: ZPFPKBXOIJYGIX-PASQLDBJSA-N

物化性质

• 沸点：
  400.5±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  isopropyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 17.17h， 生成 cleistetroside-2
  参考文献：
  名称：

  Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens

  摘要：

  A tetrasaccharide, dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-alpha-L-rhamnopyranoside (cleistetroside-2), was synthesized via '2+2' convergent strategy. Sequential regioselective 3-O-glycosylation of isopropyl 1-thio-alpha-L-rhamnopyranoside (4) with 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl trichloroacetimidate (8), and isopropyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-1-thio-rh amnopyranoside (10) with dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-2,3-O-isopropylidene-alpha-L-rharnnopyranoside (12), greatly facilitate the target availability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.05.019
• 作为产物：
  描述：

  异丙硫醇 、 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到isopropyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens

  摘要：

  A tetrasaccharide, dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-alpha-L-rhamnopyranoside (cleistetroside-2), was synthesized via '2+2' convergent strategy. Sequential regioselective 3-O-glycosylation of isopropyl 1-thio-alpha-L-rhamnopyranoside (4) with 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl trichloroacetimidate (8), and isopropyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-1-thio-rh amnopyranoside (10) with dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-2,3-O-isopropylidene-alpha-L-rharnnopyranoside (12), greatly facilitate the target availability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.05.019

文献信息

• Total synthesis of tricolorin A <i>via</i> interrupted Pummerer reaction-mediated glycosylation and one-pot relay glycosylation
  作者：Jiuchang Sun、Jing Fang、Xiong Xiao、Lei Cai、Xiang Zhao、Jing Zeng、Qian Wan

  DOI：10.1039/d0ob00513d

  日期：——

  Tricolorin A, a bioactive resin glycoside, was synthesized stepwise or in one pot based on interrupted Pummerer reaction-mediated (IPRm) glycosylation. The stepwise synthesis adopted a [2 + 2] assembly sequence, and all of the glycosidic bonds were constructed efficiently by IPRm glycosylation. The one-pot synthesis employed our recently developed one-pot relay glycosylation strategy, in which two

  基于中断的Pummerer反应介导的（IPRm）糖基化反应，逐步或在一个罐中合成了Tricolorin A（一种生物活性树脂糖苷）。逐步合成采用[2 + 2]组装顺序，并通过IPRm糖基化有效地构建了所有糖苷键。一锅合成使用我们最近开发的一锅中继糖基化策略，其中两个不同的糖苷键仅与一个当量的外部活化剂顺序连接。