allyl 2-deoxy-2-azido-4,6-benzylidene-β-D-galactopyranoside | 90405-24-6

• 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-deoxy-2-azido-4,6-benzylidene-β-D-galactopyranoside
• 英文别名: (4aR,6R,7R,8R,8aR)-7-azido-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 90405-24-6
• 化学式: C₁₆H₁₉N₃O₅
• 分子量: 333.344
• InChiKey: WOGBACPARLUOOY-XSYLOXKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2-deoxy-2-azido-4,6-benzylidene-β-D-galactopyranoside 在 咪唑 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 61.5h， 生成 allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-2-azido-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Studies Directed toward the Synthesis of Polysialogangliosides: The Regio- and Stereocontrolled Synthesis of Rationally Designed Fragments of the Tetrasialoganglioside GQ_1b⁺.

  摘要：

  The synthesis of suitably protected fragments of the tetrasialoganglioside GQ1b (I), i.e., 1 (alpha-NeuAc2 -->-8-alpha-NeuAc2 --> 3-beta-Gal1 --> 4Glc), 2 (alpha-NeuAc2 --> 8-alpha-NeuAc2 --> 3Gal), 3 (GalNAc), 4 (alpha-NeuAc2 --> 8NeuAc), 5 (beta-Gal1 -->- 3GalNAc), and 42 [beta-Gal1 --> 3-beta-GalNAc1 --> 4(alpha-NeuAc2 --> 3)beta-Gal --> 4Glc], is described. All are rationally designed so that the protecting groups can be regioselectively introduced and removed, as needed, before or after the stereoselective coupling of an appropriate pair of fragments. The syntheses of 1, 2, and 4 all feature stereoselective glycosylations by glycosyl donors that bear a C-3 thiophenoxy stereocontrolling auxiliary. Compound 3 was prepared from the D-glucosamine derivative 17 by way of a novel intramolecular nucleophilic displacement with inversion of configuration. Furthermore, model glycosylations of 4-hydroxygalactose derivatives, in which the thioglycoside 3 and the fluoride 40 served as glycosyl donors, were performed. The reaction of 3 with the glycosyl acceptor 30 gave the disaccharide 31 (GalNAc-beta-1 --> 4Gal), whereas that of 40 with 41 afforded the pentasaccharide 42.

  DOI：

  10.1021/jo00032a601
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 在 calcium sulfate 、 sodium methylate 、 对甲苯磺酸 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 33.5h， 生成 allyl 2-deoxy-2-azido-4,6-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Sabesan, Subramaniam; Lemieux, Raymond U., Canadian Journal of Chemistry, 1984, vol. 62, p. 644 - 654

  摘要：

  DOI：

文献信息

• Differentiation between Structurally Homologous Shiga 1 and Shiga 2 Toxins by Using Synthetic Glycoconjugates
  作者：Ramesh R. Kale、Colleen M. McGannon、Cynthia Fuller-Schaefer、Duane M. Hatch、Michael J. Flagler、Shantini D. Gamage、Alison A. Weiss、Suri S. Iyer

  DOI：10.1002/anie.200703680

  日期：2008.2.1
• IIJIMA, HIROYUKI;OGAWA, TOMOYA, CARBOHYDR. RES., 186,(1989) N, C. 95-106
  作者：IIJIMA, HIROYUKI、OGAWA, TOMOYA

  DOI：——

  日期：——
• NUNOMURA, SHIGEKI;MORI, MASATO;ITO, YUKISHIGE;OGAWA, TOMOYA, TETRAHEDRON LETT., 30,(1989) N8, C. 6713-6716
  作者：NUNOMURA, SHIGEKI、MORI, MASATO、ITO, YUKISHIGE、OGAWA, TOMOYA

  DOI：——

  日期：——
• NUNOMURA, SHIGEKI;MORI, MASATO;ITO, YUKISHIGE;OGAWA, TOMOYA, TETRAHEDRON LETT., 30,(1989) N1, C. 5619-5622
  作者：NUNOMURA, SHIGEKI、MORI, MASATO、ITO, YUKISHIGE、OGAWA, TOMOYA

  DOI：——

  日期：——