methyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-2-O-acetyl-6-O-benzoyl-α-D-mannopyranoside | 831210-00-5

• 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: methyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-2-O-acetyl-6-O-benzoyl-α-D-mannopyranoside
• CAS: 831210-00-5
• 化学式: C₄₂H₄₀O₁₅
• 分子量: 784.771
• InChiKey: RDZSNWZUHZNAOT-JVNSVGMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  57.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  188.65
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-2-O-acetyl-6-O-benzoyl-α-D-mannopyranoside 、 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)]-4,6-di-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)]-4,6-di-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)]-2-O-acetyl-6-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  简便地合成新孢子虫血清型B的O-去乙酰化GXM的七糖重复单元。

  摘要：

  七糖，β-D-Xylp-（1-> 2）-alpha-D-Manp-（1-> 3）-[β-D-Xylp-（1-> 2）]-alpha-D -Manp-（1-> 3）-[beta-D-GlcpA-（1-> 2）] [beta-D-Xylp-（1-> 4）]-alpha-D-Manp合成了来自新隐球菌血清B的胞外多糖的单元，作为其甲基糖苷。因此，2,3,4-三-O-苯甲酰基-β-D-吡喃并吡喃糖基-（1-> 2）-3,4,6-三-O-苯甲酰基-α-d-曼酰吡喃糖基三氯乙酰亚氨酸盐（7）和烯丙基2,3,4-三-O-苯甲酰基-β-D-吡喃喃糖基-（1→2）-4,6-二-O-苯甲酰基-α-D-甘露比山py糖（8）通过简单转化将相应的单糖衍生物偶联，得到（1-> 3）-连接的四糖9。9的脱芳基反应，然后形成三氯乙酰亚氨酸生成四糖供体11。甲基2,3，4-三-O-苯甲酰基-β-吡喃并吡喃糖基-（1→4）-

  DOI：

  10.1016/j.bmc.2004.09.049
• 作为产物：
  描述：

  methyl 2-O-acetyl-3-O-allyl-6-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 methyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->4)-2-O-acetyl-6-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  简便地合成新孢子虫血清型B的O-去乙酰化GXM的七糖重复单元。

  摘要：

  七糖，β-D-Xylp-（1-> 2）-alpha-D-Manp-（1-> 3）-[β-D-Xylp-（1-> 2）]-alpha-D -Manp-（1-> 3）-[beta-D-GlcpA-（1-> 2）] [beta-D-Xylp-（1-> 4）]-alpha-D-Manp合成了来自新隐球菌血清B的胞外多糖的单元，作为其甲基糖苷。因此，2,3,4-三-O-苯甲酰基-β-D-吡喃并吡喃糖基-（1-> 2）-3,4,6-三-O-苯甲酰基-α-d-曼酰吡喃糖基三氯乙酰亚氨酸盐（7）和烯丙基2,3,4-三-O-苯甲酰基-β-D-吡喃喃糖基-（1→2）-4,6-二-O-苯甲酰基-α-D-甘露比山py糖（8）通过简单转化将相应的单糖衍生物偶联，得到（1-> 3）-连接的四糖9。9的脱芳基反应，然后形成三氯乙酰亚氨酸生成四糖供体11。甲基2,3，4-三-O-苯甲酰基-β-吡喃并吡喃糖基-（1→4）-

  DOI：

  10.1016/j.bmc.2004.09.049

文献信息

• 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.