2-(trimethylsilyl)ethyl 2-azido-2-deoxy-β-D-galactopyranoside | 151651-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2-azido-2-deoxy-β-D-galactopyranoside
• 英文别名: 2-(Trimethylsilyl)ethyl 2-azido-2-deoxy-beta-D-galactopyranoside；(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxane-3,4-diol
• CAS: 151651-20-6
• 化学式: C₁₁H₂₃N₃O₅Si
• 分子量: 305.406
• InChiKey: GGLLUHFKNKRZOC-KAMPLNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2-azido-2-deoxy-β-D-galactopyranoside 在 三乙胺 作用下， 以 甲醇 、 对甲苯磺酸 、 2,2-二甲氧基丙烷 、 甲苯 为溶剂， 以86%的产率得到2-(Trimethylsilyl)ethyl 2-azido-2-deoxy-3,4-isopropylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Ganglioside analogs

  摘要：

  通用公式(I)的神经节苷脂内酰胺类似物衍生物，其中A是通过虚线连接到2位的公式(II)的唾液酸残基；Z.sup.1是—OH或—NHX.sup.1基团，Y.sup.30是—CH.sub.3或—CH.sub.2OH；X.sup.1和Y.sup.1共同形成键，Y.sup.2是—OH或—OR.sup.20基团，或者X.sup.1和Y.sup.2共同形成键，Y.sup.1是—OH或—NHAc；Y.sup.3是—OH或—OR.sup.20基团；R.sup.1是H或通过虚线连接到2位的公式(III)的唾液酸残基；Z.sup.2是—OH或—NHX.sup.2基团，Y.sup.30如上定义；X.sup.2和Y.sup.10共同形成键，Y.sup.20是—OH，或者X.sup.2和Y.sup.20共同形成键，Y.sup.10是—OH；但是当R.sup.1是H时，Z.sup.1是—NHX.sup.1，当R.sup.1是公式(III)的唾液酸残基时，至少一个Z.sup.1和Z.sup.2不同于—OH；R.sup.10是H，载体CA，或者基团-(糖)n。这些化合物是水解稳定的内酰胺类似物，空间上与自然发生的神经节苷脂内酯非常相似，具有抗原性，并能诱导产生与相应的神经节苷脂内酯发生交叉反应的抗体。

  公开号：

  US05637569A1
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranoside 在 甲醇 、 ether-heptane 作用下， 以 sodium methylate 为溶剂， 反应 1.5h， 以to give 24 (3.24 g, 94%), [α]D25 +8.5° (c 0.8, MeOH), m.p. 158°-161° C. (ether-heptane)的产率得到2-(trimethylsilyl)ethyl 2-azido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Ganglioside analogs

  摘要：

  公式（I）的神经节苷脂内酰胺类似物衍生物，其中A是通过虚线连接在2位的公式（II）的唾液酸残基；Z.sup.1是--OH或--NHX.sup.1基团，Y.sup.30是--CH.sub.3或--CH.sub.2 OH；X.sup.1和Y.sup.1共同形成键，Y.sup.2是--OH或--OR.sup.20基团，或者X.sup.1和Y.sup.2共同形成键，Y.sup.1是--OH或--NHAc；Y.sup.3是--OH或--OR.sup.20基团；R.sup.1是H或通过虚线连接在2位的公式（III）的唾液酸残基；Z.sup.2是--OH或--NHX.sup.2基团，Y.sup.30如上所定义；X.sup.2和Y.sup.10共同形成键，Y.sup.20是--OH，或者X.sup.2和Y.sup.20共同形成键，Y.sup.10是--OH；但是当R.sup.1是H时，Z.sup.1是--NHX.sup.1，当R.sup.1是公式（III）的唾液酸残基时，至少有一个Z.sup.1和Z.sup.2与--OH不同；R.sup.10是H、载体CA或--（糖）.sub.n基团。这些化合物是水解稳定的内酰胺类似物，空间上与天然存在的神经节苷脂内酯非常相似，具有抗原性并能够诱导产生与相应的神经节苷脂内酯交叉反应的抗体。

  公开号：

  US05637569A1

文献信息

• Arynes in the Monoarylation of Unprotected Carbohydrate Amines
  作者：Kumar Bhaskar Pal、Mukul Mahanti、Ulf J. Nilsson

  DOI：10.1021/acs.orglett.7b03741

  日期：2018.2.2

  A CsF-mediated method has been developed for the N-arylation of amino sugars that affords good to excellent yields of arylated products under mild conditions involving the in situ generation of arynes. The reaction conditions tolerate a variety of common carbohydrate protecting groups and also performs exceptionally well on unprotected amino sugar derivatives. The reactions are scalable in moderate

  已经开发出用于氨基糖的N-芳基化的CsF介导的方法，其在涉及原位生成芳烃的温和条件下提供良好至优异的芳基化产物收率。反应条件可耐受多种常见的碳水化合物保护基，并且在未保护的氨基糖衍生物上也表现出色。反应范围宽广，可以中等至良好的收率进行扩展。
• Synthesis of disaccharide glycosyl donors suitable for introduction of the β-d-Galp-(1 → 3)-α- and -β-d-Gal pNAc groups
  作者：Michael Wilstermann、Göran Magnusson

  DOI：10.1016/0008-6215(95)00026-p

  日期：1995.7

  -3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-α-d-galactopyranosyl bromide (11) in an over-all yield of 86%. Compounds 9 and 11 are suitable glycosyl donors for introduction of the β-d-Gal p-(1 → 3)-β- and -α-d-Gal pNAc groups.

  将2-（三甲基甲硅烷基）乙基2-叠氮基-4,6-O-亚苄基-2-脱氧-β-d-吡喃半乳糖苷（4）与苯基2,3,4,6-四-O-乙酰基-1-糖基化硫代-β-d-吡喃半乳糖苷得到2-（三甲基甲硅烷基）乙基2-叠氮基-4,6-O-亚苄基-2-脱氧-3-O-（2,3,4,6-四-O-乙酰基- β-d-吡喃半乳糖苷）-β-d-吡喃半乳糖苷（6），产率为99％。除去亚苄基和乙酰化得到关键中间体2-（三甲基甲硅烷基）乙基4，6-二-O-乙酰基-2-叠氮基-2-脱氧-3-O-（2,3,4,6-四- O-乙酰基-β-d-吡喃半乳糖基）-β-d-吡喃半乳糖基）（7），将其转化为甲基4,6-二-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-3-O-（2分两个步骤制备（3,4,6-四-O-乙酰基-β-d-吡喃半乳糖苷）-1-硫代-β-d-吡喃半乳糖苷（9），总产率为69％。同样地，将7分两步转化为4,6-二-O-乙
• Regioselective benzoylation of sugars mediated by excessive Bu2SnO: observation of temperature promoted migration
  作者：Zhiyuan Zhang、Chi-Huey Wong

  DOI：10.1016/s0040-4020(02)00661-0

  日期：2002.8

  Regioselective benzoylation of carbohydrates using an excess of dibutyltin oxide (Bu2SnO) at increased reaction temperatures has been developed for the synthesis of several glycoside benzoates with one or two free hydroxyl groups, including galactosides, glucosides, mannosides and lactosides in high yields. These compounds are useful as building blocks for the synthesis of complex saccharides and derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of Ganglioside Lactams Corresponding to GM1-, GM2-, GM3-, and GM4-Ganglioside Lactones
  作者：Michael Wilstermann、Leonid O. Kononov、Ulf Nilsson、Asim K. Ray、Goeran Magnusson

  DOI：10.1021/ja00122a002

  日期：1995.5

  Ganglioside lactams are potentially useful analogs of ganglioside lactones, which are highly immunogenic derivatives of gangliosides. The lactam corresponding to the G(M3)-lactone saccharide has been synthesized by sialylation of a suitably protected lactose derivative carrying an azido group in the 2'-position, followed by reduction and ring closure to form G(M3)-lactam. Glycosylation in the 4-position of the central saccharide unit gave the G(M2)- and G(M1)- lactam saccharides. By a similar route, a 2-azido-Gal derivative was sialylated and treated as above to give the G(M4)-lactam saccharide. Deprotection gave the G(M2-4)-lactam saccharides in water soluble form, whereas attempted deprotection of the G(M1)-lactam caused its degradation. The G(M3)-lactam saccharide was coupled to ceramide, to afford the ganglioside lactam analog, and via a spacer to bovine serum albumin (BSA). The BSA conjugate was used as immunogen to raise monoclonal antibodies that cross-reacted with G(M3)-lactone. The antibodies were used in a histological staining of murine melanoma cells, clearly showing the presence of G(M3)-lactone on the cell surface. Keeping the G(M2-4)-lactam saccharides in D2O at 37 degrees C for 1 month caused marginal (0-11%) hydrolysis of the lactam ring.