3,5-Di-O-benzyl-D-lyxofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-Di-O-benzyl-D-lyxofuranose
• 英文别名: (3S,4R,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolane-2,3-diol
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: LYHOPDIJCJJVNG-CJPNDHRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-Di-O-benzyl-D-lyxofuranose 在 sodium hydroxide 、 potassium tert-butylate 、 水 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.33h， 生成 1-O-methyl 3,5-di-O-benzyl β(D)xylo-pentoaldofuranose
  参考文献：
  名称：

  1,2-脱水呋喃呋喃糖苄醚的简便合成

  摘要：

  通过相应的C-1醇盐与带有甲苯磺酰氧基的C-2的分子内反应，成功地完成了1,2-脱水甘露糖基-，-lyxo-，-葡萄糖-和-xylofuranose苄基醚的合成。在相转移条件下，由相应的1,2-二醇和甲苯磺酰氯制备了关键中间体呋喃糖2-磺酸盐，收率很高。

  DOI：

  10.1016/0040-4039(94)02311-x
• 作为产物：
  描述：

  methyl 3,5-di-O-benzyl-α-D-lyxofuranoside 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以70%的产率得到3,5-Di-O-benzyl-D-lyxofuranose
  参考文献：
  名称：

  经由相应的1，2-酐将d-木糖转化为受保护的d-木糖衍生物并转化为d-木糖

  摘要：

  摘要对3,5-二-O-苄基-1,2-O-环己叉基-α-d-木呋喃糖进行酸水解得到相应的内酯，随后将其转化为3,5-二-O-苄基-2- O-甲磺酰基-d-木呋喃糖。该化合物容易与甲醇钠，苄基钠或氢氧化钠反应（大概通过相应的1,2-酐），得到保护的d-呋喃呋喃糖苷。这些化合物最终被转化为甲基α-d-lyxopyranoside或d-lyxose。

  DOI：

  10.1016/s0008-6215(99)00164-0

文献信息

• Wittig reaction with partially protected sugar lactol derivatives. Preparation of highly cytotoxic goniofufurone analogues
  作者：Velimir Popsavin、Sanja Grabež、Mirjana Popsavin、Ivana Krstić、Vesna Kojić、Gordana Bogdanović、Vladimir Divjaković

  DOI：10.1016/j.tetlet.2004.10.122

  日期：2004.12

  A new approach to the dephenyl goniofufurone analogue 2 and the corresponding (3S,4R)-stereoisomer 3 is reported. The resulting furanolactones 2 and 3 have shown a potent and selective in vitro cytotoxicity against certain human tumour cell lines.

  据报道，有一种新方法可用于脱苯古呋喃酮类似物2和相应的（3 S，4 R）-立体异构体3。所得的呋喃内酯2和3对某些人类肿瘤细胞系显示出有效的选择性体外细胞毒性。
• Synthesis and antiproliferative activity of simplified goniofufurone analogues
  作者：Bojana Sreco-Zelenovic、Sanja Grabez、Mirjana Popsavin、Vesna Kojic、Jovana Francuz、Velimir Popsavin

  DOI：10.2298/jsc200730056s

  日期：——

  Several (+)-goniofufurone analogues with simplified structures were designed, synthesized and evaluated for their in vitro antitumour activity, against a panel of human tumour cell lines. Dephenylated compounds 2 and 3 demonstrated remarkable antitumour activities, in the cultures of K562 and Raji cells with IC50 values in the range of 3.0?9.3 nM. Each of goniofufurone analogues lacking the tetrahydrofuran ring (4, 5 and 6) strongly inhibited the growth of at least one malignant cell line, with IC50 values in the range of 11-30 nM. Brief structure?activity relationship (SAR) analysis showed that the simplified goniofufurone analogues, designed by removing the phenyl group from C-7, or by opening the THF ring, could show stronger antiproliferative effects compared to control molecules. It is noticeable that analogues 2?8 are completely inactive with respect to the normal MRC-5 cell line. These findings, together with their potent antitumour activities, provide a suitable basis for the development of new and selective antitumour drugs.

  我们设计、合成了几种结构简化的 (+)-goniofufurone 类似物，并评估了它们对人类肿瘤细胞系的体外抗肿瘤活性。去苯基化合物 2 和 3 在 K562 和 Raji 细胞培养物中表现出显著的抗肿瘤活性，IC50 值在 3.0-9.3 nM 之间。缺少四氢呋喃环的每个贡碘呋喃酮类似物（4、5 和 6）都能强烈抑制至少一种恶性细胞系的生长，IC50 值在 11-30 nM 之间。简单的结构活性关系（SAR）分析表明，与对照分子相比，通过去除 C-7 上的苯基或打开四氢呋喃环而设计的简化贡碘呋喃酮类似物具有更强的抗增殖作用。值得注意的是，类似物 2?8 对正常的 MRC-5 细胞系完全无效。这些发现及其强大的抗肿瘤活性为开发新的选择性抗肿瘤药物提供了合适的基础。
• Synthesis and Glycosidic Reaction of 1,2-Anhydromanno-, Lyxo-, Gluco-, and Xylofuranose Perbenzyl Ethers
  作者：Yuguo Du、Fanzuo Kong

  DOI：10.1080/07328309608005693

  日期：1996.9

  Stereospecific synthesis of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers was successfully achieved via intramolecular S(N)2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer conditions in good yields. Condensation of the anhydro sugars with 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose or N-benzyloxycarbonyl L-serine methyl ester in the absence of catalyst gave 1,2-trans-linked glycofuranosides in high yield.
• Conversion of d-xylose to protected d-lyxose derivatives and to d-lyxose, via the corresponding 1,2-anhydride
  作者：Velimir Popsavin、Sanja Grabež、Biljana Stojanović、Mirjana Popsavin、Vjera Pejanović、Dušan Miljković

  DOI：10.1016/s0008-6215(99)00164-0

  日期：1999.9

  hydrolysis of 3,5-di- O -benzyl-1,2- O -cyclohexylidene-α- d -xylofuranose gave the corresponding lactol, which was subsequently converted to the 3,5-di- O -benzyl-2- O -mesyl- d -xylofuranose. This compound readily reacted with sodium methoxide, sodium benzylate or sodium hydroxide (presumably via the corresponding 1,2-anhydride) to give the protected d -lyxofuranosides. These compounds were finally

  摘要对3,5-二-O-苄基-1,2-O-环己叉基-α-d-木呋喃糖进行酸水解得到相应的内酯，随后将其转化为3,5-二-O-苄基-2- O-甲磺酰基-d-木呋喃糖。该化合物容易与甲醇钠，苄基钠或氢氧化钠反应（大概通过相应的1,2-酐），得到保护的d-呋喃呋喃糖苷。这些化合物最终被转化为甲基α-d-lyxopyranoside或d-lyxose。
• A facile synthesis of 1,2-anhydroglycofuranose benzyl ethers
  作者：Yuguo Du、Fanzuo Kong

  DOI：10.1016/0040-4039(94)02311-x

  日期：1995.1

  The synthesis of 1,2-anhydromanno-, -lyxo-, -gluco-, and -xylofuranose benzyl ethers was successfully achieved via intramolecular reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer condition in good yields.

  通过相应的C-1醇盐与带有甲苯磺酰氧基的C-2的分子内反应，成功地完成了1,2-脱水甘露糖基-，-lyxo-，-葡萄糖-和-xylofuranose苄基醚的合成。在相转移条件下，由相应的1,2-二醇和甲苯磺酰氯制备了关键中间体呋喃糖2-磺酸盐，收率很高。