2,6-anhydro-1,3,5-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-manno-non-8-enitol | 1311277-65-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-1,3,5-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-manno-non-8-enitol
• 英文别名: (2R,3S,4R,5S,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enyloxan-4-ol
• CAS: 1311277-65-2
• 化学式: C₃₀H₃₄O₅
• 分子量: 474.597
• InChiKey: NCYURRPBFBLOFU-XZTOTZIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-1,3,5-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-manno-non-8-enitol 在 吡啶 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 硼烷四氢呋喃络合物 、 水 、 对甲苯磺酸 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 25.83h， 生成
  参考文献：
  名称：

  Towards stable di-carba analogues of guanofosfocins

  摘要：

  Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.102
• 作为产物：
  描述：

  methyl 3-O-(4-methoxybenzyl)-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 2,6-anhydro-1,3,5-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-manno-non-8-enitol
  参考文献：
  名称：

  Towards stable di-carba analogues of guanofosfocins

  摘要：

  Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.102

文献信息

• Synthesis of a Pseudodisaccharide α-C-Glycosidically Linked to an 8-Alkylated Guanine
  作者：Mu-Hua Huang、Jan Duchek、Andrea Vasella

  DOI：10.3390/molecules18043906

  日期：——

  The synthesis of stable guanofosfocin analogues has attracted considerable attention in the past 15 years. Several guanofosfocin analogues mimicking the three constitutional elements of mannose, ribose, and guanine were designed and synthesized. Interest in ether-linked pseudodisaccharides and 8-alkylated guanines is increasing, due to their potential applications in life science. In this article,

  在过去的 15 年中，稳定鸟磷焦素类似物的合成引起了相当大的关注。设计并合成了几种模拟甘露糖、核糖和鸟嘌呤三种构成元素的鸟磷焦素类似物。由于它们在生命科学中的潜在应用，对醚连接的假二糖和 8-烷基化鸟嘌呤的兴趣正在增加。在这篇文章中，一种新的鸟磷焦素类似物 6，一种醚连接的假二糖，α-C-糖苷连接到 8-烷基化鸟嘌呤，从已知的二醇 13 以 10 长的线性步骤序列合成，总产率为 26 %。关键步骤包括环硫酸盐 8 由 7 生成的醇盐开环和 4-N-酰基-2,4-二氨基-5-亚硝基嘧啶 19 的还原环化反应形成化合物 6。
• Towards stable di-carba analogues of guanofosfocins
  作者：Jan Duchek、Mu-Hua Huang、Andrea Vasella

  DOI：10.1016/j.tetlet.2011.02.102

  日期：2011.6

  Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield. (C) 2011 Elsevier Ltd. All rights reserved.