allyl 3-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside | 612056-98-1

• 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 3-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside
• 英文别名: [(2R,4aR,6S,7S,8R,8aR)-7-hydroxy-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS: 612056-98-1
• 化学式: C₁₈H₂₂O₇
• 分子量: 350.368
• InChiKey: SBRSTZWQSHIQDH-HVKXIDHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 3-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside 在 吡啶 作用下， 以 二氯甲烷 、 水 、 三氟乙酸 为溶剂， 反应 4.0h， 生成 allyl 3-O-acetyl-2-O-chloroacetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a mannose nonasaccharide existing in the exopolysaccharide of Cryphonectria parasitica

  摘要：

  alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)[alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)]+alpha-D-Manp-(1-->6)-[alpha-D-Manp-(1-->2)]+alpha-D-Manp, existing in the exopolysaccharide of Cryphonectria parasitica was synthesized as its allyl glycoside in a regio- and stereoselective manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00267-2
• 作为产物：
  描述：

  allyl-4,6-O-benzylidene-2,3-di-O-hydroxy-D-mannopyranoside 、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以55%的产率得到allyl 3-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers

  摘要：

  我们在本文中首次报道了利用荧光标记辅助试剂和可实现自动化的 FSPE 方案合成线性和支链甘露寡糖的过程。事实证明，这种特殊的荧光连接剂能保持不断增长的寡糖链的溶解性，因此在糖基化反应和脱保护反应之间可以使用相同的反应溶剂条件和纯化方案，从而使程序适合自动化。

  DOI：

  10.1039/b803451f

文献信息

• Synthesis of a hexasaccharide, the repeating unit of O-deacetylated GXM of C. neoformans serotype A
  作者：Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/s0008-6215(03)00264-7

  日期：2003.8

  beta-D-GlcpA-(1-->2)-alpha-D-Manp-(1-->3)-[beta-D-Xylp-(1-->2)]-alpha-D-Manp-(1-->3)[-beta-D-Xylp-(1-->2)]-alpha-D-Manp, the repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar A, was synthesized as its allyl glycoside. Thus, 3-O-selective acetylation of allyl 4,6-O-benzylidene-alpha-D-mannopyranoside afforded 2, and subsequent glycosylation of 2 with 2,3,4-tri-O-benzoyl-D-xylopyranosyl trichloroacetimidate furnished the beta-(1-->2)-linked disaccharide 4. Debenzylidenation followed by benzoylation gave allyl 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->2)-3-O-acetyl-4,6-di-O-benzoyl-alpha-D-mannopyranoside (5), and selective 3-O-deacetylation gave the disaccharide acceptor 6. Coupling of 6 with 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate yielded the trisaccharide 8, and subsequent deallylation and trichloroacetimidation gave 2,3,4-tri-O-benzoyl-alpha-D-xylopyranosyl-(1-->2)-[2-O-acetyl-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->3)]-4,6-di-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (9). Condensation of the trisaccharide donor 9 with the disaccharide acceptor 6 gave the pentasaccharide 10 whose 2-O-deacetylation gave the acceptor 11. Glycosylation of 11 with methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate and subsequent deprotection gave the target hexasaccharide. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of a heptasaccharide fragment of the O-deacetylated GXM of C. neoformans serotype C
  作者：Wei Zhao、Fanzuo Kong

  DOI：10.1016/j.carres.2005.05.003

  日期：2005.7

  beta-D-Xylp-(1 -> 2)-alpha-D-Manp-(1 -> 3)-[beta-D-Xylp-(1 -> 2)][beta-D-Xylp-(1 -> 4)]-alpha-D-ManP)-(1 -> 3)-[beta-D-Xylp-(1 -> 4)]-alpha-D-Manp, the fragment of the exopolysaccharide from Cryptococcus neoformans serovar C, was synthesized as its methyl glycoside. Thus, chloro-acetylation of allyl 3 - O-acetyl-4,6- O-benzylidene-alpha-D-mannopyranoside (1) followed by debenzylidenation and selective 6-O-benzoylation afforded allyl 2-O-chloroacetyl-3-O-acetyl-6-O-benzoyl-alpha-D-mannopyranoside (4). Glycosylation of 4 with 2,3,4-tri-O-benzoyl-D-xylopyranosyl trichloroacetimidate (5) furnished the beta(1 -> 4)-linked disaccharide 6. Dechloroacetylation gave the disaccharide acceptor 7 and subsequent coupling with 5 produced the trisaccharide 8. Deacetylation of 8 gave the trisaccharide acceptor 9 and subsequent coupling with a disaccharide 10 produced the pentasaccharide 11. Reiteration of deallylation and trichloroacetimidate formation from 11 yielded the pentasaccharide donor 12. Coupling of a disaccharide acceptor 13 with 12 afforded the heptasaccharide 14. Subsequent deprotection gave the heptaoside 16, while selective 2-O-deacetylation of 14 gave the heptasaccharide acceptor 15. Condensation of 15 with glucopyranosyluronate imidate 17 did not yield the expected octaoside, instead, an orthoester product 18 was obtained. Rearrangement of 18 did not give the target octaoside; but produced 15. Meanwhile, there was no reaction between 15 and the glycosyl bromide donor 19. (c) 2005 Elsevier Ltd. All rights reserved.