1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-mannitol | 95066-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-mannitol
• 英文别名: (1S)-1-[(3aS,4R,6aR)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl]ethane-1,2-diol
• CAS: 95066-30-1
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: ISDVPTBNLSSYTA-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-mannitol 在 吡啶 、 sodium periodate 作用下， 以 乙醇 为溶剂， 生成 (1R,5S,6S)-tert-butyl 6-formyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo<3.3.0>octane-7-carboxylate
  参考文献：
  名称：

  Potent competitive inhibition of α-galactosidase and α-glucosidase activity by 1,4-dideoxy-1,4-iminopentitols: syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol and of both enantiomers of 1,4-dideoxy-1,4-iminoarabinitol

  摘要：

  DOI：

  10.1016/s0040-4039(00)98636-2
• 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 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 127.5h， 生成 1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-mannitol
  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。
• Derivatives of 1,4-dideoxy-1,4-imino-D-mannitol and a process for their
  申请人：Monsanto Company

  公开号：US04996329A1

  公开（公告）日：1991-02-26

  Novel derivatives of 1,4-dideoxy-1,4-imino-D-mannitol and method for their synthesis from 4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol or its triflate derivative are disclosed. The novel derivatives, 6-fluoro-1,4-imino-1,4,6-trideoxy-D-mannitol and the N-butyl and N-benzyl derivatives of 1,4-dideoxy-1,4-amino-D-mannitol, have useful mannosidase inhibitory activity.

  本发明揭示了从4,5-脱水-1-偶氮-1-脱氧-2,3-O-异丙基亚甲基-D-他利醇或其三氟甲磺酸盐衍生物合成的1,4-脱氧-1,4-亚胺-D-甘露醇的新衍生物及其合成方法。这些新的衍生物包括6-氟-1,4-亚胺-1,4,6-脱氧-D-甘露醇以及N-正丁基和N-苄基衍生物的1,4-脱氧-1,4-氨基-D-甘露醇，具有有用的甘露糖苷酶抑制活性。
• 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。
• Synthesis of some polyhydroxylated pyrrolidine derivatives.
  作者：HIROYUKI SETOI、HIROSHI KAYAKIRI、HIDEKAZU TAKENO、MASASHI HASHIMOTO

  DOI：10.1248/cpb.35.3995

  日期：——

  Polyhydroxylated pyrrolidine derivatives, 7, 11, 15, and 18, were synthesized from 4, a. key intermediate for our total synthesis of swainsonine (1). The immunostimulating activities of these new derivatives were found to be moderate and less than that of swainsonine.

  聚羟基吡咯烷衍生物7、11、15和18由4合成，4是我们全合成斯温森碱（1）的关键中间体。这些新衍生物的免疫刺激活性适中，低于斯温森碱。
• Synthesis of 1,4-dideoxy-1,4-imino-D-mannitol
  申请人：MONSANTO COMPANY

  公开号：EP0424349A1

  公开（公告）日：1991-04-24

  Swainsonine and analogs, namely, 1,4-­dideoxy-1,4-imino-D-mannitol and the novel ring contracted swainsonines, (1S,2R,7R,7aR)-1,2-trihydroxypyrrolizidine and (1SD,2R,7S,7aR)-1,2,-7-trihydroxypyrrolizidine, are synthesized from the divergent intermediate, 4,5-­anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-­talitol. These novel compounds are glycosidase inhibitors.

  Swainsonine及其类似物，即1,4-二脱氧-1,4-亚胺-D-甘露醇和新型环收缩的Swainsonine，(1S,2R,7R,7aR)-1,2-三羟基吡咯烷和(1SD,2R,7S,7aR)-1,2,-7-三羟基吡咯烷，均由分支中间体4,5-脱水-1-叠氮-1-脱氧-2,3-O-异丙基-D-甘露醇合成。这些新化合物是糖苷酶抑制剂。