(2R,3S,4R,1'S)-3,4-dihydroxy-2-1',2'-dihydroxyethylpyrrolidine | 95189-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3S,4R,1'S)-3,4-dihydroxy-2-1',2'-dihydroxyethylpyrrolidine
• 英文别名: 1,4-dideoxy-1,4-imino-D-mannitol；1,4-dideoxy-1,4-imino-L-gulitol；1,4-Dideoxy-1,4-iminomannitol；swainsonine；1,4-dideoxy-1,4-imini-D-mannitol；(2R,3S,4R)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol
• CAS: 95189-02-9
• 化学式: C₆H₁₃NO₄
• 分子量: 163.174
• InChiKey: RVNSAAIWCWTCTJ-KVTDHHQDSA-N

物化性质

• 熔点：
  125-128 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• 沸点：
  448.6±40.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D-甘露糖 在 钯 吡啶 、 咪唑 、 sodium tetrahydroborate 、 sodium azide 、 3 A molecular sieve 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 、 乙酰氯 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 重水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 175.5h， 生成 (2R,3S,4R,1'S)-3,4-dihydroxy-2-1',2'-dihydroxyethylpyrrolidine
  参考文献：
  名称：

  Synthesis of the α-Mannosidase inhibitors swainsonine [(1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine] and 1,4-dideoxy-1,4-imino-d-mannitol from mannose

  摘要：

  DOI：

  10.1016/s0040-4020(01)86850-2

文献信息

• Synthesis of the mannosidase inhibitors swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol and of the ring contracted swainsonines, (1S, 2R, 7R, 7aR)-1,2,7-trihydroxypyrrolizidine and (1S, 2R, 7S, 7aR)-1,2,7-trihydroxypyrrolizidine
  作者：Neil M. Carpenter、George W.J. Fleet、Isabelle Cenci di Bello、Bryan Winchester、Linda E. Fellows、Robert J. Nash

  DOI：10.1016/s0040-4039(01)93953-x

  日期：1989.1

  4,5-Anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol is a divergent intermediate for the efficient and practical syntheses of 1,4-dideoxy-1,4-imino-D-mannitol, swainsonine and of the ring contracted swainsonines, (1S, 2R, 7R, 7aR)-1,2,7-trihydroxypyrrolizidine and (1S, 2R, 7S, 7aR)-1,2,7-trihydroxypyrrolizidine. The effect on glycosidases of the ring contracted swainsonines is reported.

  4,5-脱水-1-叠氮基-1-脱氧-2,3-O-异亚丙基-D-塔罗糖醇是一种高效有效合成1,4-二脱氧-1,4-亚氨基-D-的异体中间体甘露醇，swainsonine和环收缩的swainsonines中的（1S，2R，7R，7aR）-1,2,7-三羟基吡咯烷并（1S，2R，7S，7aR）-1,2,7-三羟基吡咯烷并。据报道，收缩的swainsonines对糖苷酶的作用。
• [EN] CONJUGATE<br/>[FR] CONJUGUÉ
  申请人：GLYKOS BIOMEDICAL OY

  公开号：WO2019243672A1

  公开（公告）日：2019-12-26

  A conjugate is disclosed. The conjugate may comprise a targeting unit for delivery to a tumour, and a glycosylation inhibitor for inhibiting glycosylation in the tumour, thereby decreasing the immunosuppressive activity of the tumour. The glycosylation inhibitor may be conjugated to the targeting unit.

  揭示了一种共轭物。该共轭物可能包括用于传递至肿瘤的靶向单元，以及用于抑制肿瘤中的糖基化的糖基化抑制剂，从而降低肿瘤的免疫抑制活性。糖基化抑制剂可以与靶向单元结合。
• Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars
  作者：Bao-Chen Qian、Akiko Kamori、Kyoko Kinami、Atsushi Kato、Yi-Xian Li、George W. J. Fleet、Chu-Yi Yu

  DOI：10.1039/c6ob00531d

  日期：——

  Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-D-mannitol) was the acetonation of D-mannose.

  N-羟基吡咯烷环的C5通过区域选择性氧化成硝酮然后进行非对映选择性还原的差向异构化提供了一种合成swainsonine和相关化合物的新方法。在有效的甘露糖苷酶抑制剂DIM（1,4- dideoxy -1,4- imino - D-甘露醇）的合成中唯一的保护是D-甘露糖的乙酰化。
• [EN] STABILE CONJUGATE<br/>[FR] CONJUGUÉ STABLE
  申请人：GLYKOS BIOMEDICAL OY

  公开号：WO2021123506A1

  公开（公告）日：2021-06-24

  A conjugate is disclosed. The conjugate may be represented by Formula I: [D-O-L]n-T Formula I wherein D is a payload molecule; O is an oxygen atom of said payload molecule; T is a targeting unit capable of binding a target molecule, cell and/or tissue; and n is at least 1.

  本发明揭示了一种共轭物。该共轭物可以用公式I表示：[D-O-L]n-T 公式I，其中D是荷载分子；O是所述荷载分子的氧原子；T是能够结合目标分子、细胞和/或组织的靶向单元；n至少为1。
• Design synthesis and preliminary evaluation of a potent α- mannosidase inhibitor: 1,4-dideoxy-1,4-imino-<scp>D</scp>-mannitol
  作者：George W. J. Fleet、Paul W. Smith、Stephen V. Evans、Linda E. Fellows

  DOI：10.1039/c39840001240

  日期：——

  1,4-Dideoxy-1,4-imino-D-mannitol (1), synthesised from benzyl α-D-mannopyranoside, is a potent competitive inhibitor of the hydrolysis of p-nitrophenyl α-D-mannopyranoside catalysed by Jack Bean α-mannosidase (Cnavalia ensiformis); this is the first report of the specific inhibition of a glycosidase by a pyrrolidine analogue of a furanose sugar.

  1,4-二脱氧-1,4-亚氨基d -mannitol（1）中，从合成的苄基α- d -mannopyranoside，是水解的有效竞争性抑制剂p硝基苯基α- d -mannopyranoside由刀豆α催化的-甘露糖苷酶（Cnavalia ensiformis）；这是呋喃糖的吡咯烷类似物特异性抑制糖苷酶的首次报道。