2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate | 432519-15-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
• CAS: 432519-15-8
• 化学式: C₄₄H₄₀Cl₃NO₁₄
• 分子量: 913.159
• InChiKey: TVPMJJVCWQJLEI-YEZSGFMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  62.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  192.27
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate 在 1,8-diaza-bicyclo[5.4.0]undecene 、 三氟甲磺酸三甲基硅酯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1-> 3)-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of a hexasaccharide fragment of group E streptococci polysaccharide and the tetrasaccharide repeating unit of E. coli O7:K98:H6

  摘要：

  Syntheses of a hexasaccharide, the dimer of the repeating unit of the group E streptococci polysaccharide, and a tetrasaccharide, the repeating unit of the E. coli 07:K98:H6, were achieved by constructing alternate alpha-L-(l --> 2)- and alpha-L-(1 --> 3)linked L-rhamnopyranose backbones and substituting with beta-linked D-glucopyranose side chains for the former, and a D-gluco-pyranosyluronate branch for the latter, respectively, at O-2 of the L-rhamnose ring. (C) 2004 Elsevier Ltd. All rights reserved.Syntheses of a hexasaccharide, the dimer of the repeating unit of the group E streptococci polysaccharide, and a tetrasaccharide, the repeating unit of the E. coli O7:K98:H6, were achieved by constructing alternate alpha-L-(1 --> 2)- and alpha-L-(1 --> 3)-linked L-rhamnopyranose backbones and substituting with P-linked D-glucopyranose side chains for the former, and a D-gluco-pyranosyluronate branch for the latter, respectively, at O-2 of the L-rhamnose ring. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.027
• 作为产物：
  描述：

  allyl 4-O-benzoyl-α-L-rhamnopyranoside 在 1,8-diaza-bicyclo[5.4.0]undecene 、 三氟甲磺酸三甲基硅酯 、 palladium dichloride 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of a hexasaccharide fragment of group E streptococci polysaccharide and the tetrasaccharide repeating unit of E. coli O7:K98:H6

  摘要：

  Syntheses of a hexasaccharide, the dimer of the repeating unit of the group E streptococci polysaccharide, and a tetrasaccharide, the repeating unit of the E. coli 07:K98:H6, were achieved by constructing alternate alpha-L-(l --> 2)- and alpha-L-(1 --> 3)linked L-rhamnopyranose backbones and substituting with beta-linked D-glucopyranose side chains for the former, and a D-gluco-pyranosyluronate branch for the latter, respectively, at O-2 of the L-rhamnose ring. (C) 2004 Elsevier Ltd. All rights reserved.Syntheses of a hexasaccharide, the dimer of the repeating unit of the group E streptococci polysaccharide, and a tetrasaccharide, the repeating unit of the E. coli O7:K98:H6, were achieved by constructing alternate alpha-L-(1 --> 2)- and alpha-L-(1 --> 3)-linked L-rhamnopyranose backbones and substituting with P-linked D-glucopyranose side chains for the former, and a D-gluco-pyranosyluronate branch for the latter, respectively, at O-2 of the L-rhamnose ring. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.027

文献信息

• Synthesis of an xylosylated rhamnose pentasaccharide, the repeating unit of the O-chain polysaccharide of the lipopolysaccharide of Xanthomonas campestris pv. begoniae GSPB 525
  作者：Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/s0008-6215(01)00330-5

  日期：2002.3

  A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1 --> 3)-[beta-L-Xylp-(1 --> 2)-]-alpha-L-Rhap-(1 --> 3)-[beta-L-Xylp-(1 --> 4)]-L-Rhap, the repeating unit of the O-chain polysaccharide (OPS) of the lipo polysaccharides of Xanthomonas campestris pv. begoniae GSPB 525 was synthesized by a highly regio- and stereoselective way. Thus coupling of 1.2-O-ethylidene-beta-L-rhamnopyranose (1) with 2.3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (2) to give (1 --> 3)-linked disaccharide (3), subsequent benzoylation. deethylidenation, acetylation, 1-O-deacetylation, and trichloroacetimidation afforded the disaccharide donor 11. Condensation of 11 with 1 yielded 2.3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-2-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-1.2-O-ethylidene-beta-L-rhamnopyranose (12), and selective deacetylation of 12 yielded the trisaccharide diol acceptor 15. Coupling of 15 with 2.3.4-tri-O-benzoyl-alpha-L-xylopyranosyl trichloroacetimidate (16), followed by deprotection, gave the target pentasaccharide 19. (C) 2002 Elsevier Science Ltd. All rights reserved.