allyl 3-O-acetyl-2-O-chloroacetyl-α-D-mannopyranoside | 612057-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-acetyl-2-O-chloroacetyl-α-D-mannopyranoside
• CAS: 612057-00-8
• 化学式: C₁₃H₁₉ClO₈
• 分子量: 338.742
• InChiKey: HTJQANPSRUWZBL-WSLQDRLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.65
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  allyl 3-O-acetyl-2-O-chloroacetyl-α-D-mannopyranoside 在 吡啶 、 2,4-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-3-O-acetyl-6-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a heptasaccharide fragment of the O-deacetylated GXM of C. neoformans serotype C

  摘要：

  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.

  DOI：

  10.1016/j.carres.2005.05.003
• 作为产物：
  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

文献信息

• Convergent synthesis of a galactofuranosylated mannan, the repeating unit of Trichophyton mentagrophytes IFO 5466 and Trichophyton rubrum IFO 5467
  作者：Zuchao Ma、Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/j.tetasy.2004.03.041

  日期：2004.5

  An undecasaccharide repeating unit of the polysaccharide of Trichophyton mentagrophytes IFO 5466 and Trichophyton rubrum IFO 5467, alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-[beta-D-Galf-(1 --> 3)]-alpha-D-Manp-(1 --> 2)-[beta-D-Galf-(1 --> 3)]-alpha-D-Manp(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(1 --> 2)-[beta-D-Galf-(1 --> 3)]-Manp was synthesized as its allyl glycoside by coupling of a octasaccharide trichloroacetimidate donor 19 with a trisaccharide acceptor 28. The donor 19 and 28 were obtained with allyl 3-O-acetyl-2-O-betizoyl-alpha-D-mannopyranoside 2, allyl 3-O-acetyl-4,6-di-O-benzoyl-alpha-D-mannopyranoside 9, allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2)-3,4,6-tri-O-belizoyl-alpha-D-mannopyranoside 13, 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate 26 and 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuraliosyl trichloroacetimidate 16 as the key synthons by appropriate combination through simple transformation. (C) 2004 Elsevier Ltd. All rights reserved.