4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-β-D-glucopyranosyl)-1,2-O-(R,S)-ethylidene-α-D-glucopyranose | 205690-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-β-D-glucopyranosyl)-1,2-O-(R,S)-ethylidene-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(3aR,5R,6R,7S,7aR)-6-acetyloxy-2-methyl-7-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methoxy]-3,4,5-triacetyloxyoxan-2-yl]methyl 2-chloroacetate
• CAS: 205690-40-0
• 化学式: C₃₈H₅₁ClO₂₅
• 分子量: 943.261
• InChiKey: HGUSKXLCLDJRIF-FTBTYOSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  64
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  301
• 氢给体数：
  0
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-β-D-glucopyranosyl)-1,2-O-(R,S)-ethylidene-α-D-glucopyranose 在 硫脲 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-1,2-O-(S)-ethylidene-α-D-glucopyranose 、 4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-1,2-O-(R)-ethylidene-α-D-glucopyranose
  参考文献：
  名称：

  高度收敛和有效合成植物抗毒素诱导剂六糖。

  摘要：

  过乙酰化的六糖1,2,4-三-O-乙酰基-3-O-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-6-O-（2,3， 4-三-O-乙酰基-6-O-（2,4-二-O-乙酰基-3,6-二-O-（2,3,4,6-四-O-乙酰基1-β-D β-D-吡喃葡萄糖基）-β-D-吡喃葡萄糖基）-β-D-吡喃葡萄糖基）-β-D-吡喃葡萄糖基21以分块方式合成，使用三糖三氯乙酰亚氨酸2,4-二-O-乙酰基-3,6 -二-O-（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-α-D-吡喃葡萄糖基三氯乙酰亚氨酸酯17作为糖基供体，三糖4-O-乙酰基-3-O -（2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基）-6-O-（2,3,4-三-O-乙酰基-β-D-吡喃葡萄糖基）-1,2 -O-（R，S）亚乙基-α-D-吡喃葡萄糖酮18作为受体。供体17和受体18易于由三糖3-O-（2,3,4,6-

  DOI：

  10.1016/s0008-6215(99)00003-8
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-α-D-glucopyranose 1,2-{6-O-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-β-D-glucopyranosyl)-4-O-acetyl-1,2-O-ethylidene-α-D-glucopyranos}-3-yl orthoacetate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以76%的产率得到4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-acetyl-6-O-chloroacetyl-β-D-glucopyranosyl)-1,2-O-(R,S)-ethylidene-α-D-glucopyranose
  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。
• A highly convergent synthesis of the phytoalexin elicitor hexasaccharide
  作者：Wei Wang、Fanzuo Kong

  DOI：10.1016/s0040-4039(98)00087-2

  日期：1998.4

  A highly convergent synthesis of the elicitor-active D-glucohexatose 1 and its variant 19 was achieved via coupling of the trisaccharide donor 14 with the trisaccharide acceptor 15 followed by deprotection. 14 and 15 were obtained from rearrangement of the orthoesters 6 and 5 respectively which were prepared quantitatively from coupling of the disaccharide 4 with acetobromoglucose and 6-O-chloroacetylated

  通过三糖供体14与三糖受体15的偶联然后脱保护，实现了激发子活性D-葡萄糖己糖1及其变体19的高度收敛的合成。分别由原酸酯6和5的重排获得14和15，其分别由二糖4分别与乙酰溴葡萄糖和6-O-氯乙酰化乙酰溴葡萄糖偶联而定量制备。