allyl 3-O-benzoyl-4,6-di-O-benzylidene-α-D-mannopyranoside | 743431-96-1

• 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-benzoyl-4,6-di-O-benzylidene-α-D-mannopyranoside
• 英文别名: allyl 3-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside；allyl 4,6-O-benzylidene-3-O-benzoyl-α-D-mannopyranoside；[(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] benzoate
• CAS: 743431-96-1
• 化学式: C₂₃H₂₄O₇
• 分子量: 412.439
• InChiKey: OLZJMMIKJIGGML-WFTGQSOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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-benzoyl-4,6-di-O-benzylidene-α-D-mannopyranoside 在 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 20.0h， 生成 allyl 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 6)-3,4-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi

  摘要：

  Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2' of the mannose residue attached to the core mannose residue by (1 --> 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 --> 6)-linked tetra-saccharide backbone 26 with 2-, 2"-O-ClAc, and 2'-, 2"'-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.012
• 作为产物：
  描述：

  苯甲酰氯 、 allyl 4,6-O-benzylidene-α-D-mannopyranoside 在 二甲基二氯化锡 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 以1.66 g的产率得到allyl 3-O-benzoyl-4,6-di-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  二等分N-乙酰氨基葡萄糖（GlcNAc）-N-聚糖的聚合合成

  摘要：

  二等分N的化学合成通过[4 + 2]和[6 + 2]糖基化的融合合成途径，获得了含-乙酰氨基葡萄糖（GlcNAc）的N-聚糖。尽管由于糖基化位点的空间位阻和缺乏邻近基团的参与，关键的糖基化在产量和选择性方面都具有挑战性，但是这种合成路线减少了反应步骤的数量。通过通过醚配位稳定氧碳鎓离子中间体，可以提高这些糖基化的收率。探索了糖基供体保护基团，以通过操纵远程参与来实现完美的α选择性。研究了四糖与两个二糖的同时糖基化作用，以有效地构建一个两等分的含GlcNAc的N-聚糖。

  DOI：

  10.1002/asia.201800367

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
• 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）-
• Synthesis of a unique mannose α-1-phosphate side chain moiety found in Candida auris cell wall mannan
  作者：Zuchao Ma、Harry E. Ensley、Bridget Graves、Michael D. Kruppa、Peter J. Rice、Douglas W. Lowman、David L. Williams

  DOI：10.1016/j.carres.2024.109059

  日期：2024.3

  therapeutics, diagnostic tools and/or research reagents that target . Herein, we describe the successful synthesis and structural characterization of a Manα1PO-containing disaccharide moiety that mimics the phosphomannan found in . Additionally, we present evidence that the synthetic Manα1PO glycomimetic is specifically recognized and bound by cell surface pattern recognition receptors, rhDectin-2, rhMannose

  是一种新兴的真菌病原体，已成为全球公共卫生威胁。尽管对其他物种细胞壁的性质、组成和结构进行了大量研究，但对细胞壁的了解却少之又少。我们已经证明细胞壁甘露聚糖含有独特的磷酸甘露聚糖结构，该结构将甘露聚糖与其他真菌物种中发现的甘露聚糖区别开来。具体而言，它具有其他真菌甘露聚糖和真菌病原体中不存在的两种独特的酸不稳定甘露糖 α-1-磷酸 (Manα1PO) 侧链。这种独特的甘露聚糖结构特征为开发针对 的疫苗、治疗剂、诊断工具和/或研究试剂提供了机会。在此，我们描述了含有 Manα1PO 的二糖部分的成功合成和结构表征，该二糖部分模仿了 中发现的磷酸甘露聚糖。此外，我们提供的证据表明，合成的 Manα1PO 糖模拟物可被细胞表面模式识别受体 rhDectin-2、rhMannose 受体和 rhMincle 特异性识别和结合，这些受体已知在针对以及其他真菌病原体的先天免疫反应中发挥重要作用。 Manα1PO
• Convergent Synthesis of a Bisecting<i>N</i>-Acetylglucosamine (GlcNAc)-Containing N-Glycan
  作者：Yoshiyuki Manabe、Hiroki Shomura、Naoya Minamoto、Masahiro Nagasaki、Yohei Takakura、Katsunori Tanaka、Alba Silipo、Antonio Molinaro、Koichi Fukase

  DOI：10.1002/asia.201800367

  日期：2018.6.18

  owing to steric hindrance at the glycosylation site and a lack of neighboring group participation. The yields of these glycosylations were enhanced by stabilizing the oxocarbenium ion intermediate through ether coordination. Glycosyl donor protecting groups were explored in an effort to realize perfect α selectivity by manipulating remote participation. The simultaneous glycosylations of a tetrasaccharide

  二等分N的化学合成通过[4 + 2]和[6 + 2]糖基化的融合合成途径，获得了含-乙酰氨基葡萄糖（GlcNAc）的N-聚糖。尽管由于糖基化位点的空间位阻和缺乏邻近基团的参与，关键的糖基化在产量和选择性方面都具有挑战性，但是这种合成路线减少了反应步骤的数量。通过通过醚配位稳定氧碳鎓离子中间体，可以提高这些糖基化的收率。探索了糖基供体保护基团，以通过操纵远程参与来实现完美的α选择性。研究了四糖与两个二糖的同时糖基化作用，以有效地构建一个两等分的含GlcNAc的N-聚糖。
• Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi
  作者：Zuchao Ma、Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/j.carres.2004.04.012

  日期：2004.7

  Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2' of the mannose residue attached to the core mannose residue by (1 --> 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranosyl-(1 --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 --> 6)-linked tetra-saccharide backbone 26 with 2-, 2"-O-ClAc, and 2'-, 2"'-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation. (C) 2004 Elsevier Ltd. All rights reserved.