3-O-benzyl-6,7-dideoxy-1:2-O-isopropylidene-7-(phthalimido)-α-D-xylo-heptofuranos-5-ulose | 725707-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-O-benzyl-6,7-dideoxy-1:2-O-isopropylidene-7-(phthalimido)-α-D-xylo-heptofuranos-5-ulose
• 英文别名: 2-[3-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-oxopropyl]isoindole-1,3-dione
• CAS: 725707-71-1
• 化学式: C₂₅H₂₅NO₇
• 分子量: 451.476
• InChiKey: VVXJWWLUDIUTNH-OOICKAIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-6,7-dideoxy-1:2-O-isopropylidene-7-(phthalimido)-α-D-xylo-heptofuranos-5-ulose 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以66%的产率得到7-amino-3-O-benzyl-6,7-dideoxy-1:2-O-isopropylidene-α-D-xylo-heptofuranos-5-ulose hydrazone
  参考文献：
  名称：

  Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic amounts of TMSOTf

  摘要：

  The O-phthalimidomethyl trichloroacetimidate (1), as a latent aminomethylating agent, exhibits high electrophilicity towards a variety of C-nucleophiles in the presence of catalytic amounts of TMSOTf and mild reaction conditions. The nucleophiles include aromatics, alkenes and active methylene compounds 2-11 whereby a phthalimidomethyl group could be introduced to give compounds 12-22. Removal of the phthaloyl group gave the respective amines, beta-amino ketones, and beta-amino acids. The O-(trichloroacetamido)methyl trichloroacetimidate (35) was also found to be a good amidomethylating agent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.011
• 作为产物：
  描述：

  [1-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-vinyloxy]-trimethyl-silane 、 O-phthalimidomethyl trichloroacetamidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以87%的产率得到3-O-benzyl-6,7-dideoxy-1:2-O-isopropylidene-7-(phthalimido)-α-D-xylo-heptofuranos-5-ulose
  参考文献：
  名称：

  Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic amounts of TMSOTf

  摘要：

  The O-phthalimidomethyl trichloroacetimidate (1), as a latent aminomethylating agent, exhibits high electrophilicity towards a variety of C-nucleophiles in the presence of catalytic amounts of TMSOTf and mild reaction conditions. The nucleophiles include aromatics, alkenes and active methylene compounds 2-11 whereby a phthalimidomethyl group could be introduced to give compounds 12-22. Removal of the phthaloyl group gave the respective amines, beta-amino ketones, and beta-amino acids. The O-(trichloroacetamido)methyl trichloroacetimidate (35) was also found to be a good amidomethylating agent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.011

文献信息

• Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic amounts of TMSOTf
  作者：Ibrahim A.I Ali、El Sayed H El Ashry、Richard R Schmidt

  DOI：10.1016/j.tet.2004.04.011

  日期：2004.5

  The O-phthalimidomethyl trichloroacetimidate (1), as a latent aminomethylating agent, exhibits high electrophilicity towards a variety of C-nucleophiles in the presence of catalytic amounts of TMSOTf and mild reaction conditions. The nucleophiles include aromatics, alkenes and active methylene compounds 2-11 whereby a phthalimidomethyl group could be introduced to give compounds 12-22. Removal of the phthaloyl group gave the respective amines, beta-amino ketones, and beta-amino acids. The O-(trichloroacetamido)methyl trichloroacetimidate (35) was also found to be a good amidomethylating agent. (C) 2004 Elsevier Ltd. All rights reserved.