(1R)-1-C-[1-(N-tert-butyloxycarbonyl)aminocyclopropyl]-1,2-O-isopropylidene-D-threitol | 1203660-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-C-[1-(N-tert-butyloxycarbonyl)aminocyclopropyl]-1,2-O-isopropylidene-D-threitol
• CAS: 1203660-96-1
• 化学式: C₁₅H₂₇NO₆
• 分子量: 317.382
• InChiKey: PJDASMBSYVCVMM-VWYCJHECSA-N

反应信息

• 作为反应物：
  描述：

  (1R)-1-C-[1-(N-tert-butyloxycarbonyl)aminocyclopropyl]-1,2-O-isopropylidene-D-threitol 在 silica-supported NaIO₄ 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(2R,3R,4R)-N-tert-butyloxycarbonyl-3,4-O-isopropylidene-5-spirocyclopropyl-2,3,4-trihydroxypyrrolidine
  参考文献：
  名称：

  The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors

  摘要：

  Nitrogen-in-the-ring analogues of L-fucose and L-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile as the key step. Four new spirocyclopropyl iminosugar analogues were generated, which displayed some activity towards L-fucosidase and L-rhamnosidase. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.010
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (1R)-1-C-(1-aminocyclopropyl)-1,2-O-isopropylidene-D-threitol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到(1R)-1-C-[1-(N-tert-butyloxycarbonyl)aminocyclopropyl]-1,2-O-isopropylidene-D-threitol
  参考文献：
  名称：

  The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors

  摘要：

  Nitrogen-in-the-ring analogues of L-fucose and L-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile as the key step. Four new spirocyclopropyl iminosugar analogues were generated, which displayed some activity towards L-fucosidase and L-rhamnosidase. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.010