methyl 2-O-methyl-α-L-fucose | 99603-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-methyl-α-L-fucose
• 英文别名: methyl 2-O-methyl-L-fucopyranoside；methyl O²-methyl-α-L-6-deoxy-galactopyranoside；(2S,3S,4R,5S,6R)-5,6-dimethoxy-2-methyloxane-3,4-diol
• CAS: 99603-80-2
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: ZIRPXMSHWUAJJI-FMGWEMOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  methyl 2-O-methyl-α-L-fucose 在 platinum(IV) oxide 吡啶 、 盐酸羟胺 、 氢气 、 溴 、 二正丁基氧化锡 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 5.5h， 生成 methyl 4-acetamido-3-O-acetyl-4,6-dideoxy-2-O-methyl-α-L-galactopyranoside
  参考文献：
  名称：

  Structures of the glycopeptidolipid antigens of serovars 25and 26 of the Mycobacterium aviumserocomplex, synthesis of allyl glycosides of the outer disaccharide units and serology of the derived neoglycoproteins

  摘要：

  The pentasaccharide hapten released from the glycopeptidolipid (GPL) antigen of M. avium serovar 26 has been characterized as O-(2,4-di-O-methyl-alpha-L-fucopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose. The allyl glycosides of the outer glycosyl and glycobiosyl units of this hapten have been synthesized, the latter by a route involving oxidation of the corresponding D-glucopyranose derivative. Conjugation of allyl glycosides to protein by ozonolysis and reductive coupling afforded neoantigens (neo 26-1 and 26-2), both of which interacted with antibodies to M. avium serovar 26. The terminal sugar residue of the pentasaccharide hapten of the serovar 25 GPL had been shown to have the galacto configuration on the basis of H-1-C-13 NMR correlation spectroscopy, but absolute configurational assignment for the sugar awaited the synthesis, as for neo 26, of two glycobiosyl NGPs bearing the terminal sugar in the D and L enantiomeric forms, respectively. Only the glycobiosyl NGP bearing the terminal sugar as the D-enantiomer interacted with antibodies to M. avium serovar 25, thus providing evidence for the absolute configuration of the sugar, and showing that the complete oligosaccharide hapten has the structure, O-(4-acetamido-4,6-dideoxy-2-O-methyl-alpha-D-galactopyranosyl)-(1 --> 4)-O-beta-D-glucopyranosyluronic acid-(1 --> 4)-O-(2-O-methyl-alpha-L-fucopyranosyl)-(1 --> 3)-O-alpha-L-rhamnopyranosyl-(1 --> 2)-6-deoxy-L-talose.

  DOI：

  10.1016/s0008-6215(92)84233-i
• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-α-L-fucopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 methyl 2-O-methyl-α-L-fucose
  参考文献：
  名称：

  碘鎓离子辅助合成的四聚体片段，对应于堪萨斯分枝杆菌血清II和IV的细胞壁酚糖脂

  摘要：

  含间隔基的四聚体3和4，堪萨斯分枝杆菌血清型II和IV的酚糖脂衍生物是通过碘离子介导的三聚体受体4- [2-（苄氧基羰基氨基）乙基]苯基（2）与1-乙基的甘露糖基化反应制得的。硫代d-D-吡喃甘露糖苷供体7，13，和24。此外，供体的糖基化特性7，13，24，29-31，每个包含一个不同的保护基团在2位，通过用模型受体执行缩合检查18（L）和其对映体18（d）。

  DOI：

  10.1016/0040-4020(96)00034-8

文献信息

• Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid
  作者：Evgeny V. Evtushenko

  DOI：10.1016/s0008-6215(99)00044-0

  日期：1999.3

  Abstract Partial methylation of the methyl pyranosides of a number of pentoses, hexoses, 6-deoxyhexoses, methyl uronates and their methyl ethers with diazomethane in the presence of transition-metal chlorides and boric acid was studied. It was found for methyl glycosides of pentoses and 6-deoxyhexoses that tin(II), antimony(III), and titanium(IV) chlorides as well as boric acid promoted substitution

  摘要研究了在过渡金属氯化物和硼酸存在下，许多戊糖，己糖，6-脱氧己糖，尿酸甲酯及其甲基醚的甲基吡喃糖苷与重氮甲烷的部分甲基化。发现戊糖和6-脱氧己糖的甲基糖苷中锡（II），锑（III）和钛（IV）氯化物以及硼酸主要促进OH-3的取代，但被铈（III）和锌的取代（II）观察到盐主要取代了OH-2。在所有情况下，甲基β-1-鼠李糖吡喃糖苷的甲基化表现出较高的OH-2反应性。在氯化锡（II），锑（III）和铈（III）的存在下，己糖甲基糖苷的甲基化反应主要产生了3-甲基醚。不参与进一步络合的3-甲基醚 积聚高达50-80％的反应混合物（95％至100％的单甲醚馏分）。建议用于许多糖的方便的甲基醚的合成。
• Studies on the koenigs-knorr reaction
  作者：Marta Dejter-Juszynski、Harold M. Flowers

  DOI：10.1016/s0008-6215(00)82857-8

  日期：1973.5

  Abstract Partial benzylation of methyl 2- O -benzyl-α- L -fucopyranoside afforded a mixture of methyl 2,3-, and 2,4-di- O -benzyl-α- L -fucopyranoside which were separated by means of their monoacetates. Partial benzylation of methyl α- L -fucopyranoside gave the 2,4-, and 3,4-dibenzyl ethers in the ratio of 3:2, and no 2,3-isomer could be detected in the reaction mixture. The structures of the three

  摘要2- O-苄基-α-L-呋喃果糖苷甲基的部分苄基化反应得到甲基2,3-和2,4-二-O-苄基-α-L-呋喃果糖苷的混合物，通过单乙酸酯进行分离。甲基α-L-呋喃果糖苷的部分苄基化得到2：4-和3,4-二苄基醚的比例为3：2，并且在反应混合物中未检测到2,3-异构体。确定了三种二苄基醚的结构：（a）通过分析其乙酸盐的nmr光谱，和（b）通过甲基化，通过氢解去除苄基和表征甲基糖苷的甲基醚。这些化合物的酸水解得到L-岩藻糖的单甲基醚，其中两个与已知化合物相同，而第三个4-O-甲基-L-岩藻糖是新化合物。2,3-的选择性对硝基苯甲酰化 2,4-和3,4-二-O-苄基-L-岩藻糖，然后乙酰化并在二氯甲烷中用溴化氢处理，得到三种可能的单-O-乙酰基-二-O-苄基-α-L -呋喃果糖基溴化物，其与苄基2-乙酰氨基-3,4-二-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖苷缩合。衍生自2-O-乙酰基取代的
• New syntheses of methyl ethers from methyl ?-L-fucopyranoside
  作者：E. V. Evtushenko、A. I. Kalinovskii、Yu. S. Ovodov

  DOI：10.1007/bf00574194

  日期：——

  A method for obtaining methyl esters of methyl α-L-fucopyranoside based on the partial methylation of methyl α-L-fucopyranoside with the subsequent liquid and gasliquid chromatography of the methyl ethers is described. Their properties are given.

  描述了基于甲基 α-L-吡喃岩藻糖苷的部分甲基化以及随后的甲基醚的液相和气液色谱获得甲基 α-L-吡喃岩藻糖苷甲酯的方法。给出了它们的属性。
• Nikrad, P. V.; Beierbeck, H.; Lemieux, R. U., Canadian Journal of Chemistry, 1992, vol. 70, # 1, p. 241 - 253
  作者：Nikrad, P. V.、Beierbeck, H.、Lemieux, R. U.

  DOI：——

  日期：——
• Jayalakshmi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 11, p. 1087 - 1089
  作者：Jayalakshmi

  DOI：——

  日期：——