benzyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside | 105285-86-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside
• 英文别名: [(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] benzoate
• CAS: 105285-86-7
• 化学式: C₂₃H₂₆O₆
• 分子量: 398.456
• InChiKey: FAIQSWFGIWYPDV-OUNJQYEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 硫脲 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 22.92h， 生成 benzyl (2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Oligomerization of a rhamnanic trisaccharide repeating unit of O-chain polysaccharides from phytopathogenic bacteria

  摘要：

  An efficient synthesis of a protected trisaccharide building block alpha-L-Rha(1-->3)-alpha-L-Rha(1-->2)-alpha-L-Rha related to the structure of many lipopolysaccharide 0-chains from phytopathogenic bacteria has been developed. The protecting group pattern consisting of benzoyl, benzyl and chloroacetyl groups facilitated the use of the trisaccharide building block in the synthesis of two higher oligomers, an oligorhamnosyl hexasaccharide and a nonasaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02237-2
• 作为产物：
  描述：

  benzyl α-L-rhamnopyranoside 在 吡啶 、 对甲苯磺酸 作用下， 反应 2.0h， 生成 benzyl 4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  Oligomerization of a rhamnanic trisaccharide repeating unit of O-chain polysaccharides from phytopathogenic bacteria

  摘要：

  An efficient synthesis of a protected trisaccharide building block alpha-L-Rha(1-->3)-alpha-L-Rha(1-->2)-alpha-L-Rha related to the structure of many lipopolysaccharide 0-chains from phytopathogenic bacteria has been developed. The protecting group pattern consisting of benzoyl, benzyl and chloroacetyl groups facilitated the use of the trisaccharide building block in the synthesis of two higher oligomers, an oligorhamnosyl hexasaccharide and a nonasaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02237-2

文献信息

• Ziegler, Thomas, Angewandte Chemie, 1992, vol. 104, # 10, p. 1369 - 1371
  作者：Ziegler, Thomas

  DOI：——

  日期：——
• Synthesis of disaccharide analogues of methyl 4-O-α-d-galactopyranosyl-β-d-galactopyranoside (“methyl urobioside”), the minimum structure recognised by p-fimbriated E. coli
  作者：Thomas Norberg、Stefan Oscarson、Szönyi Maria

  DOI：10.1016/s0008-6215(00)90311-2

  日期：1986.9