allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside | 95068-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• 英文别名: allyl 2-N-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside；N-[(4aR,6R,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 95068-66-9
• 化学式: C₁₄H₂₃NO₆
• 分子量: 301.34
• InChiKey: IDMODUZZHWSKOL-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 在 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 2-N-acetyl-1-O-3-(2-aminoethyl-thio)propyl-β-muramoyl-L-alanyl-D-isoglutamine trifluoroacetate
  参考文献：
  名称：

  肽聚糖衍生的新糖肽聚合物的合成和促炎作用。

  摘要：

  DOI：

  10.1021/ja0104655
• 作为产物：
  描述：

  3-O-acetyl-2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X

  摘要：

  本发明涉及从糖类衍生的化合物，其重现志贺氏菌弗氏菌血清型3a和X的表位，并且涉及将其用于制备疫苗组合物。更具体地，本发明涉及包括下文描述的寡糖或多糖的新型糖结合化合物，用于合成这些寡糖或多糖和糖结合物的方法，这些寡糖或多糖的衍生物，含有这些衍生物的组合物，以及将糖结合物用于疫苗目的的用途。最后，本发明涉及使用一个或多个寡糖或多糖或其结合物诊断志贺氏菌弗氏菌感染的方法。

  公开号：

  US08815239B2

文献信息

• Synthesis of Two Tetra- and Four Pentasaccharide Fragments of<i>Shigella flexneri</i>Serotypes 3a and X O-Antigens from a Common Tetrasaccharide Intermediate
  作者：Julien Boutet、Laurence A. Mulard

  DOI：10.1002/ejoc.200800693

  日期：2008.11

  Ac→2]-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→}n ((E)ABAcCD)n polymer were synthesized as their propyl glycosides by use of a common fully protected (E)ABAcC intermediate (9). Tetrasaccharide 9 derived from the condensation of an EA donor and a BAcC acceptor. Partial and full deprotection gave free tetrasaccharides (E)ABAcC and (E)ABC, respectively. Alternatively, 9 was converted into a trichloroacetimidate

  所得受体与 D 供体的糖基化，以及随后的部分或全部脱保护，得到支链五糖 D(E)ABAcC 和 D(E)ABC。所有目标都是志贺氏菌 3a 的 O 抗原的一部分，这是一种流行的血清型。非 O-乙酰化寡糖由 S.flexneri 血清型 X O-抗原共有。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Synthesis of 5-Thio-<scp>l</scp>-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-<scp>l</scp>-Fucosidases
  作者：Masayuki Izumi、Osamu Tsuruta、Satoru Harayama、Hironobu Hashimoto

  DOI：10.1021/jo961725h

  日期：1997.2.1

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.
• Efficient route to orthogonally protected precursors of 2-acylamino-2-deoxy-3-O-substituted-β-d-glucopyranose derivatives and use thereof
  作者：Julien Boutet、Tae Hee Kim、Catherine Guerreiro、Laurence A. Mulard

  DOI：10.1016/j.tetlet.2008.06.052

  日期：2008.9

  An efficient route to two 3-O-acyl-2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-D-glucopyranosyl trichloroacetimidate donors is reported. As demonstrated for the 3-O-acetyl derivative, these building blocks are exquisite beta-D-glucosamine donors when reacted either with simple alcohols or with complex oligosaccharides. Besides, their protection pattern is compatible with selective deprotection and subsequent chain elongation at O-3 of the newly incorporated glucosamine residue. (C) 2008 Elsevier Ltd. All rights reserved.
• Efficient and stereoselective 1,2-cis glycoside formation of 5-thioaldopyranoses: glycosylation with peracetylated 5-thio-D- arabinopyranosyl and 5-thio-L-fucopyranosyl trichloroacetimidates
  作者：Hironobu Hashimoto、Masayuki Izumi

  DOI：10.1016/s0040-4039(00)74054-8

  日期：1993.7

  Trichloroacetimidate method was proved to be effective for 5-thio-D-arabinopyranosylation and 5-thio-L-fucopyranosylation of N-acetyl-D-glucosaminides and D-galactosides. In these 5-thioglycosylation the neighboring group participation of 2-0-acetyl function was not decisive of anomeric stereoselectivity to give 1,2-cis pseudodisaccharides predominantly. Allyl 2-O-(5-thio-alpha-L-fucopyranosyl)-beta-D-galactopyranoside showed potent inhibitory activity toward alpha-L-fucosidase (Ki = 30muM).