(1R,2S,3S,4R)-5-hydroxymethyl-1-octylamino-2,3,4-trihydroxycyclohex-5-ene | 177898-42-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3S,4R)-5-hydroxymethyl-1-octylamino-2,3,4-trihydroxycyclohex-5-ene
• 英文别名: N-octyl-β-valienamine；(1s,2s,3r,6r)-4-(Hydroxymethyl)-6-(Octylamino)cyclohex-4-Ene-1,2,3-Triol
• CAS: 177898-42-9
• 化学式: C₁₅H₂₉NO₄
• 分子量: 287.4
• InChiKey: UPZUHYMBTUUPML-KBXIAJHMSA-N

物化性质

• 沸点：
  449.2±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4R)-5-hydroxymethyl-1-octylamino-2,3,4-trihydroxycyclohex-5-ene 在 盐酸 作用下， 以 水 为溶剂， 以100%的产率得到N-octyl-β-valienamine hydrochloride
  参考文献：
  名称：

  Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV)

  摘要：

  (+)-原儿茶糖苷醇(1)和(-)-威博儿茶糖苷醇(2)，这两种糖苷均可以通过肌醇的生物转化简便制备，成功转化为了相应的4-甲基环己-5-烯-1,2,3-三醇衍生物。研究证明，这些化合物在保留其构型的情况下，适合作为具有生物活性的氨基糖（如强效化学伴侣药物候选物N-辛基-4-表-β-戊吡胺醇(3)和N-辛基-β-戊吡胺醇(4)）的前体。 (以上译文仅供参考，英文原文版权为2011 Elsevier Ltd.所有，保留所有权利。)

  DOI：

  10.1016/j.bmcl.2011.09.067
• 作为产物：
  描述：

  (1R,2S,3R)-4-(acetoxymethyl)-6-bromocyclohex-4-ene-1,2,3-triyl triacetate 在 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 (1R,2S,3S,4R)-5-hydroxymethyl-1-octylamino-2,3,4-trihydroxycyclohex-5-ene
  参考文献：
  名称：

  Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV)

  摘要：

  (+)-原儿茶糖苷醇(1)和(-)-威博儿茶糖苷醇(2)，这两种糖苷均可以通过肌醇的生物转化简便制备，成功转化为了相应的4-甲基环己-5-烯-1,2,3-三醇衍生物。研究证明，这些化合物在保留其构型的情况下，适合作为具有生物活性的氨基糖（如强效化学伴侣药物候选物N-辛基-4-表-β-戊吡胺醇(3)和N-辛基-β-戊吡胺醇(4)）的前体。 (以上译文仅供参考，英文原文版权为2011 Elsevier Ltd.所有，保留所有权利。)

  DOI：

  10.1016/j.bmcl.2011.09.067

文献信息

• Novel stereoselective syntheses of <i>N</i>-octyl-β-valienamine (NOV) and <i>N</i>-octyl-4-<i>epi</i>-β-valienamine (NOEV) from (−)-shikimic acid
  作者：Feng-Lei Li、Jiang-Ping Yu、Wei Ding、Mian-Mian Sun、Yun-Gang He、Xing-Liang Zhu、Shi-Ling Liu、Xiao-Xin Shi

  DOI：10.1039/c9ra09235h

  日期：——

  N-Octyl-β-valienamine (NOV) 1 and N-octyl-4-epi-β-valienamine (NOEV) 2 are potent chemical chaperone drug candidates for the therapy of lysosomal storage disorders. Novel stereoselective syntheses of NOV 1 and NOEV 2 starting from naturally abundant (−)-shikimic acid are described in this article. The common key intermediate compound 5 was first synthesized from readily available (−)-shikimic acid

  N -Octyl-β-valienamine (NOV) 1和N -octyl-4- epi -β-valienamine (NOEV) 2是治疗溶酶体贮积症的有效化学伴侣药物候选者。本文描述了从天然丰富的 (-)-莽草酸开始的 NOV 1和 NOEV 2的新型立体选择性合成。常见的关键中间体化合物5首先由现成的 (-)-莽草酸通过9 个步骤合成，产率为 50%。然后化合物5通过5 个步骤以 61% 的产率转化为 NOEV 1 ，它也通过以下途径转化为 NOEV 2 8 步，收率 38%。总之，NOV 1是通过14 个步骤合成的，总产率为 31%；NOEV 2通过17 个步骤合成，总产率为 19%。
• ACID ADDITION SALT OF CARBASUGAR AMINE DERIVATIVE
  申请人：SEIKAGAKU CORPORATION

  公开号：EP1632476B1

  公开（公告）日：2013-01-02
• Synthesis of potent β-D-glucocerebrosidase inhibitors: N-alkyl-β-valienamines
  作者：Seiichiro Ogawa、Makoto Ashiura、Chikara Uchida、Shinsuke Watanabe、Chihiro Yamazaki、Kiwamu Yamagishi、Jin-ichi Inokuchi

  DOI：10.1016/0960-894x(96)00146-1

  日期：1996.4

  Six homologous derivatives (N-butyl 3a, hexyl 3b, octyl 3c, decyl 3d, tetradecyl 3e and stearyl 3f) of beta-valienamine were synthesized. All have been shown to be potent and specific inhibitors of beta-glucocerebrosidase, and to have no potency against glucosylceramide synthase (mouse liver microsomes). Among them, the N-octyl derivative possesses the strongest activity (IC50 3 x 10(-8) M), being almost 10-fold more potent compared to the unsaturated 5a-carba-glucosylceramide 1. Compounds 3b and 3e are also moderate inhibitors of alpha-glucosidase (Baker's yeast). Copyright (C) 1996 Elsevier Science Ltd
• REGULATED BIOCIRCUIT SYSTEMS
  申请人：Obsidian Therapeutics, Inc.

  公开号：US20190192691A1

  公开（公告）日：2019-06-27

  The present invention provides regulatable biocircuit systems. Such systems provide modular and tunable protein expression systems in support of the discovery and development of therapeutic modalities.
• IDENTIFICATION AND TARGETED MODULATION OF GENE SIGNALING NETWORKS
  申请人：CAMP4 THERAPEUTICS CORPORATION

  公开号：US20210254056A1

  公开（公告）日：2021-08-19

  The present invention provides methods and compositions for the evaluation, alteration and/or optimization of gene signaling. Methods and systems are also provided which exploit the information generated in the identification of new targets and non-canonical signaling pathways.