allyl 3-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside
• 英文别名: Allyl 3-O-benzyl-2-O-chloroacetyl-a-L-rhamnopyranoside；[(2R,3R,4R,5S,6S)-5-hydroxy-6-methyl-4-phenylmethoxy-2-prop-2-enoxyoxan-3-yl] 2-chloroacetate
• 化学式: C₁₈H₂₃ClO₆
• 分子量: 370.83
• InChiKey: WDNLGWSGAATPDS-KMJFJPQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 3-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside 、 异丁酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到allyl 2-O-chloroacetyl-3-O-benzyl-4-O-isobutyryl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthetic studies on the trisaccharide intermediate of resin glycoside merremoside H2

  摘要：

  A protected trisaccharide imidate, 2,3-di-O-acetyl-4,6-O-benzylidene-beta-D-glucopyranosyl-(1 -> 3)-2-O-chloroacetyl-3-O-benzyl-4-isobutyryl-alpha-L-rhamnopyranosyl-(1 -> 4)-2-O-isobutyryl-alpha-L-rhamnopyranosyl trichloroacetimidate (1), has been synthesized by a block synthesis approach. Compound 1 can serve as a key intermediate in the total synthesis of resin glycoside merremoside H-2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.08.005
• 作为产物：
  描述：

  氯乙酰氯 、 烯丙基 3-O-苄基-alpha-L-吡喃鼠李糖苷 在 potassium iodide 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以68%的产率得到allyl 3-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-α-l-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D

  摘要：

  The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1. 1 equiv of acyl chloride in the presence of 1. 5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.001

文献信息

• Synthetic studies on the trisaccharide intermediate of resin glycoside merremoside H2
  作者：Xiao-Qiu Shen、Lin Xie、Liang Gao、Li-Li He、Qian Yang、Jin-Song Yang

  DOI：10.1016/j.carres.2009.08.005

  日期：2009.10

  A protected trisaccharide imidate, 2,3-di-O-acetyl-4,6-O-benzylidene-beta-D-glucopyranosyl-(1 -> 3)-2-O-chloroacetyl-3-O-benzyl-4-isobutyryl-alpha-L-rhamnopyranosyl-(1 -> 4)-2-O-isobutyryl-alpha-L-rhamnopyranosyl trichloroacetimidate (1), has been synthesized by a block synthesis approach. Compound 1 can serve as a key intermediate in the total synthesis of resin glycoside merremoside H-2. (C) 2009 Elsevier Ltd. All rights reserved.
• Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-α-l-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D
  作者：Qian Yang、Ming Lei、Qin-Jian Yin、Jin-Song Yang

  DOI：10.1016/j.carres.2007.03.001

  日期：2007.7

  The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1. 1 equiv of acyl chloride in the presence of 1. 5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D. (C) 2007 Elsevier Ltd. All rights reserved.