methyl 2-azido-4,6-benzylidene-2-deoxy-α-D-galactopyranoside | 362651-60-3

• 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: methyl 2-azido-4,6-benzylidene-2-deoxy-α-D-galactopyranoside
• 英文别名: (4aR,6S,7R,8R,8aR)-7-azido-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 362651-60-3
• 化学式: C₁₄H₁₇N₃O₅
• 分子量: 307.306
• InChiKey: WCSBCLMCXJSBOJ-CQMHSGHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-4,6-benzylidene-2-deoxy-α-D-galactopyranoside 在 吡啶 、 4 A molecular sieve 作用下， 以 水 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 1.75h， 生成 methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Bukowski, Ralph; Morris, Laura M.; Woods, Robert J., European Journal of Organic Chemistry, 2001, # 14, p. 2697 - 2705

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-α/β-D-galactopyranosyl nitrate 在 sodium 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 109.0h， 生成 methyl 2-azido-4,6-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Bukowski, Ralph; Morris, Laura M.; Woods, Robert J., European Journal of Organic Chemistry, 2001, # 14, p. 2697 - 2705

  摘要：

  DOI：

文献信息

• Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
  作者：Jing Fang、Ting Li、Xiang Ma、Jiuchang Sun、Lei Cai、Qi Chen、Zhiwen Liao、Lingkui Meng、Jing Zeng、Qian Wan

  DOI：10.1016/j.cclet.2021.06.069

  日期：2022.1

  The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of

  描述了一种在无过渡金属条件下参与烷基化和芳基化的锍叶立德。不同的反应模式允许单独激活非叶立基S-烷基和S-芳基键。在酸性条件下，锍叶立德用作促进烷基化的烷基阳离子前体。而在碱性条件下，非叶立基 S-芳基键的断裂可有效地产生O-芳基化化合物。协议的稳健性是由包括碳水化合物在内的各种底物的出色兼容性建立的。
• Synthesis of a Natural Oligosaccharide Antibiotic Active against <i>Helicobacter pylori</i>
  作者：Shino Manabe、Kazuyuki Ishii、Yukishige Ito

  DOI：10.1021/jo070669p

  日期：2007.8.1

  An oligosaccharide active against Helicobacter pylori was synthesized in a highly efficient manner for the first time. The anti-H. pylori oligosaccharide structure is a core-2 branched-type oligosaccharide with a characteristic alpha-N-acetylglucosamine at the nonreducing end. The oligosaccharide was synthesized from the nonreducing end to the reducing end, with an N-benzyl-2,3-oxazolidinone-carrying glycosyl donor used to introduce an alpha-N-acetylglucosamine at the nonreducing end. Complete chemoselective activation of a bromo sugar in the presence of a thioglycoside acceptor was achieved, and the use of 2,6-dimethylphenyl thioglycoside prevented the aglycon transfer observed when the corresponding phenyl thioglycoside is used as an acceptor.
• Bukowski, Ralph; Morris, Laura M.; Woods, Robert J., European Journal of Organic Chemistry, 2001, # 14, p. 2697 - 2705
  作者：Bukowski, Ralph、Morris, Laura M.、Woods, Robert J.、Weimar, Thomas

  DOI：——

  日期：——