allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)-4,6-di-O-benzoyl-α-D-mannopyranoside | 612064-53-6

• 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: allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)-4,6-di-O-benzoyl-α-D-mannopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Xyl(b1-2)[Bz(-4)][Bz(-6)]Man(a)-O-allyl；[(2R,3S,4S,5S,6S)-3-benzoyloxy-4-hydroxy-6-prop-2-enoxy-5-[(2S,3R,4S,5R)-3,4,5-tribenzoyloxyoxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 612064-53-6
• 化学式: C₄₉H₄₄O₁₅
• 分子量: 872.879
• InChiKey: BJIYEAPYHNYPHB-GDDJEAIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  64
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 、 allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)-4,6-di-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到allyl 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-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：

  allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)-3-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside 在 甲醇 、 乙酰氯 作用下， 以 二氯甲烷 、 水 、 甲苯 、 三氟乙酸 为溶剂， 反应 12.0h， 生成 allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->2)-4,6-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a hexasaccharide, the repeating unit of O-deacetylated GXM of C. neoformans serotype A

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(03)00264-7

文献信息

• Synthesis of a hexasaccharide fragment of the O-deacetylated GXM of C. neoformans serotype B
  作者：Wei Zhao、Fanzuo Kong

  DOI：10.1016/j.carres.2004.04.010

  日期：2004.7

  beta-(1-->4)-linked disaccharide 6. Deallylation followed by trichloroacetimidate formation gave the disaccharide donor 8, and subsequent coupling with allyl 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->2)-4,6-di-O-benzoyl-alpha-D-mannopy ranoside (9), produced the tetrasaccharide 10. Reiteration of deallylation and trichloroacetimidate formation from 10 yielded the tetrasaccharide donor 12. The downstream disaccharide

  beta-D-Xylp-（1-> 4）-alpha-D-Manp-（1-> 3）-[beta-D-Xylp-（1-> 2）]-alpha-D-Manp-合成了（1-> 3）-β-D-Xylp-（1-> 2）]-α-D-Manp，它是来自新隐球菌血清B的胞外多糖片段，作为其甲基糖苷。因此，对烯丙基3-O-苯甲酰基-4,6-O-亚苄基-α-D-甘露吡喃糖苷（1）进行乙酰化，然后进行脱苄基化和选择性6-O-苯甲酰化，得到烯丙基2-O-乙酰基-3,6-di -O-苯甲酰基-α-D-甘露吡喃糖苷（4）。用2,3,4-三-O-苯甲酰基-D-吡喃喃糖基三氯乙酰亚氨酸盐（5）对4进行糖基化，得到β-（1-> 4）连接的二糖6。并随后与烯丙基2,3,4-三-O-苯甲酰基-β-D-吡喃吡喃糖基-（1-> 2）-4,6-二-O-苯甲酰基-α-D-甘露糖核苷（9） ，产生四糖10。从10重复脱羧和形成三氯乙亚氨酸
• 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.
• Facile synthesis of the heptasaccharide repeating unit of O-deacetylated GXM of C. neoformans serotype B
  作者：Wei Zhao、Fanzuo Kong

  DOI：10.1016/j.bmc.2004.09.049

  日期：2005.1

  repeating unit of the exopolysaccharide from Cryptococcus neoformans serovar B, was synthesized as its methyl glycoside. Thus 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-d-mann opyranosyl trichloroacetimidate (7) and allyl 2,3,4-tri-O-benzoyl-beta-D-xylopyranosyl-(1-->2)-4,6-di-O-benzoyl-alpha-D-mannopy ranoside (8), readily obtained from the corresponding monosaccharide derivatives

  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）-