isopropyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside | 946499-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(3aR,4S,6S,7S,7aR)-4-[(2S,3S,4R,5R,6S)-3,5-diacetyloxy-2-methyl-6-propan-2-ylsulfanyloxan-4-yl]oxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
• CAS: 946499-69-0
• 化学式: C₂₄H₃₈O₁₁S
• 分子量: 534.625
• InChiKey: BIBULJYPJQISDI-FOHVCIMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  isopropyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 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：

  4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.67h， 生成 isopropyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-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