dodecanyl 4-O-acetyl-2,3-di-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside | 946499-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodecanyl 4-O-acetyl-2,3-di-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• CAS: 946499-70-3
• 化学式: C₄₁H₈₀O₁₀Si₂
• 分子量: 789.251
• InChiKey: PHTPXQHMZDYCRW-JTNXOHILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.03
• 重原子数：
  53.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  100.14
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  dodecanyl 4-O-acetyl-2,3-di-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以70%的产率得到dodecanyl 4-O-acetyl-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-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
• 作为产物：
  描述：

  1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 在 吡啶 、 咪唑 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 29.67h， 生成 dodecanyl 4-O-acetyl-2,3-di-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-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