甲基 6-脱氧-2-O-甲基-alpha-D-吡喃半乳糖苷 | 59981-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基 6-脱氧-2-O-甲基-alpha-D-吡喃半乳糖苷
• 中文别名: 甲基6-脱氧-2-O-甲基-α-D-吡喃半乳糖苷
• 英文名称: methyl 2-O-methyl-α-D-fucopyranoside
• 英文别名: 2-O-methyl-α-D-fucopyranoside；Methyl 6-Deoxy-2-O-methyl-alpha-D-galactopyranoside；(2R,3R,4S,5R,6S)-5,6-dimethoxy-2-methyloxane-3,4-diol
• CAS: 59981-27-0
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: ZIRPXMSHWUAJJI-HNEXDWKRSA-N

物化性质

• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

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：

  甲基 6-脱氧-2-O-甲基-alpha-D-吡喃半乳糖苷 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 2.5h， 生成 (2R,4S,5R,6S)-3-Amino-5,6-dimethoxy-2-methyl-tetrahydro-pyran-4-ol
  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-2-O-methyl-α-D-fucopyranoside 在 硫酸 作用下， 反应 5.0h， 生成 甲基 6-脱氧-2-O-甲基-alpha-D-吡喃半乳糖苷
  参考文献：
  名称：

  Synthesis of methyl 2,3-, 2,4- and 3,4-di-O-methyl-.ALPHA.-D-fucopyranosides.

  摘要：

  甲基2,3-(15),2,4-(11)和3,4-二-O-甲基-α-D-吡喃岩藻糖苷（8）是通过甲基3,4-O-异亚丙基-α-D-吡喃岩藻糖苷从甲基α-D-吡喃岩藻糖苷制备的。这些物质是含D-岩藻糖残基皂苷甲基化分析所必需的。化合物8和11在开始这项工作之前尚未合成。

  DOI：

  10.1248/cpb.28.632

文献信息

• Iodonium ion-assisted synthesis of tetrameric fragments corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovars II and IV
  作者：Korien Zegelaar-Jaarsveld、Howard I. Duynstee、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0040-4020(96)00034-8

  日期：1996.3

  The spacer-containing tetramers 3 and 4, derivatives of the phenolic glycolipids of Mycobacterium kansasii serovars II and IV were prepared by iodonium ion-mediated mannosylation of trimeric acceptor 4-[2-(benzyloxycarbonylamino)ethyl]phenyl (2) with ethyl 1-thio-d-mannopyranoside donors 7, 13, and 24. In addition, the glycosylating properties of donors 7, 13, 24, 29–31, each containing a different

  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）。