3',4'-di-O-acetyl-6'-O-chloroacetyl-α-D-glucopyranose 1',2'-(1,2-O-ethylidene-α-D-glucopyranos-6-yl orthoacetate) | 230953-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3',4'-di-O-acetyl-6'-O-chloroacetyl-α-D-glucopyranose 1',2'-(1,2-O-ethylidene-α-D-glucopyranos-6-yl orthoacetate)
• 英文别名: [(3aR,5R,6R,7S,7aR)-2-[[(3aR,5R,6S,7S,7aR)-6,7-dihydroxy-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methoxy]-6,7-diacetyloxy-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl 2-chloroacetate
• CAS: 230953-14-7
• 化学式: C₂₂H₃₁ClO₁₅
• 分子量: 570.932
• InChiKey: GMYMJWDCDGIQLZ-AFPRFPOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3',4'-di-O-acetyl-6'-O-chloroacetyl-α-D-glucopyranose 1',2'-(1,2-O-ethylidene-α-D-glucopyranos-6-yl orthoacetate) 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到3,4-di-O-acetyl-6-O-chloroacetyl-α-D-glucopyranose 1,2-(3,4-di-O-acetyl-1,2-O-ethylidene-α-D-glucopyranos)-6-yl orthoacetate
  参考文献：
  名称：

  Facile Syntheses of the Trisaccharide Acceptors—The Key Intermediates for Assembling the Elicitor Hexasaccharide

  摘要：

  A facile synthesis of trisaccharide 7, the key intermediate for assembling phytoalexin glucohexatose elicitor, was achieved via orthoester formation-rearrangement from stepwise coupling of 1,2-O-ethylidene-alpha-D-glucopyranose (2) with 2, 3,4-tri-O-acetyl-6-O-chloroacetyl-alpha-D-glucopyranosyl bromide at 6-position and with acetobromoglucose at 3-position respectively. Similar strategy was used for the synthesis of 14.

  DOI：

  10.1080/00397919908085942
• 作为产物：
  描述：

  1,2-O-ethylidene(R,S)-α-D-glucopyranose 、 2,3,4-tri-O-acetyl-6-O-chloroacetyl-α-D-glucopyranosyl bromide 在 2,4-二甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以82%的产率得到3',4'-di-O-acetyl-6'-O-chloroacetyl-α-D-glucopyranose 1',2'-(1,2-O-ethylidene-α-D-glucopyranos-6-yl orthoacetate)
  参考文献：
  名称：

  Facile Syntheses of the Trisaccharide Acceptors—The Key Intermediates for Assembling the Elicitor Hexasaccharide

  摘要：

  A facile synthesis of trisaccharide 7, the key intermediate for assembling phytoalexin glucohexatose elicitor, was achieved via orthoester formation-rearrangement from stepwise coupling of 1,2-O-ethylidene-alpha-D-glucopyranose (2) with 2, 3,4-tri-O-acetyl-6-O-chloroacetyl-alpha-D-glucopyranosyl bromide at 6-position and with acetobromoglucose at 3-position respectively. Similar strategy was used for the synthesis of 14.

  DOI：

  10.1080/00397919908085942

文献信息

• Highly Regio- and Stereoselective Synthesis of Bioactive Oligosaccharides Using 1,2-<i>O</i>-Ethylidene-α-<scp>d</scp>-gluco- and -β-<scp>d</scp>-Mannopyranose as the Acceptors and Acetobromosugars as the Donors via Ortho Ester Intermediates
  作者：Wei Wang、Fanzuo Kong

  DOI：10.1021/jo982508e

  日期：1999.7.1

  This paper presents a new, and effective method for highly regio- and stereoselective synthesis of oligosaccharides with 1,2-trans linkages using 1,2-O-ethylidenated gluco- and mannopyranose as the acceptors and simple acetobromosugars as the glycosyl donors through ortho ester formation-rearrangement strategy. Biologically important 3,6-branched oligosaccharides such as the phytoalexin elicitor hexasaccharide

  本文提出了一种以 1,2-O-亚乙基化葡萄糖和吡喃甘露糖为受体，以简单的乙酰溴糖为糖基供体通过原酸酯高度区域选择性和立体选择性合成具有 1,2-反式键的寡糖的新方法。形成重排策略。生物学上重要的 3,6-支链寡糖，如植物抗毒素诱导剂六糖和结合 ConA 的 3,6-支链甘露三糖很容易通过新方法以高产率合成。