allyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-α-D-mannopyranoside | 631918-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-α-D-mannopyranoside
• 英文别名: allyl 2,3-di-O-acetate-4,6-O-benzylidene-α-D-mannopyranoside
• CAS: 631918-98-4
• 化学式: C₂₀H₂₄O₈
• 分子量: 392.406
• InChiKey: BBEBRAONRZZYPM-JWLCQNFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-α-D-mannopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 allyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-4,6-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  A practical synthesis of α-d-Manp-(1→3)-α-d-Manp-(1→2)-[α-d-Glcp-(1→3)]-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp, an O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c

  摘要：

  An O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c, alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->2)-[alpha-D-Glcp(1-->3)] alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp was synthesized as its methyl glycoside. Acetylation of allyl 4,6-O-benzylidene-alpha-D-mannopyranoside, followed by debenzylidenization and benzoylation gave allyl 2,3-di-O-acetyl-4,6-di-O-benzoyl-alpha-D-mannopyranoside (3), and subsequent deacetylation of 3 with CH3COCl-MeOH gave the monosaccharide acceptor 4. Condensation of isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside (6) with 4 selectively afforded the alpha-(l-->3)-linked disaccharide 7. Condensation of 7 with the (1-->3)-linked disaccharide donor 9, followed by deallylation and trichloroacetimidation, afforded the tetrasaccharide donor 12. Coupling of 12 with disaccharide acceptor 13, followed by debenzylation and deacylation, furnished the target heterohexasaccharide 16. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00381-1
• 作为产物：
  描述：

  乙酸酐 、 allyl 4,6-O-benzylidene-α-D-mannopyranoside 在 吡啶 作用下， 以95%的产率得到allyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  A practical synthesis of α-d-Manp-(1→3)-α-d-Manp-(1→2)-[α-d-Glcp-(1→3)]-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp, an O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c

  摘要：

  An O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c, alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->2)-[alpha-D-Glcp(1-->3)] alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp was synthesized as its methyl glycoside. Acetylation of allyl 4,6-O-benzylidene-alpha-D-mannopyranoside, followed by debenzylidenization and benzoylation gave allyl 2,3-di-O-acetyl-4,6-di-O-benzoyl-alpha-D-mannopyranoside (3), and subsequent deacetylation of 3 with CH3COCl-MeOH gave the monosaccharide acceptor 4. Condensation of isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside (6) with 4 selectively afforded the alpha-(l-->3)-linked disaccharide 7. Condensation of 7 with the (1-->3)-linked disaccharide donor 9, followed by deallylation and trichloroacetimidation, afforded the tetrasaccharide donor 12. Coupling of 12 with disaccharide acceptor 13, followed by debenzylation and deacylation, furnished the target heterohexasaccharide 16. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00381-1

文献信息

• Ceric ammonium nitrate/acetic anhydride: A tunable system for the <i>O</i>-acetylation and mononitration of diversely protected carbohydrates
  作者：Mohindra Seepersaud、Savita Seecharan、Lorale J. Lalgee、Nigel Kevin Jalsa

  DOI：10.1080/00397911.2016.1230219

  日期：2017.5.3

  ABSTRACT Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the esterified products being furnished in good yields. Apart from affording the O-acetylated products, their mononitrated counterparts were also

  摘要 使用乙酸酐和催化量的硝酸铈铵 (CAN) 实现了多种部分保护的碳水化合物衍生物的酯化。证明了与常用保护基团的相容性，酯化产物以良好的产率提供。除了提供 O-乙酰化产物外，还产生了它们的单硝化对应物，这取决于起始材料的反应性。降低 CAN 的摩尔当量只能提供 O-乙酰化产物，而增加它有利于单硝化衍生物。图形概要