(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-methylcyclohex-4-ene-1,2,3-triol | 1229922-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-methylcyclohex-4-ene-1,2,3-triol
• 英文别名: N-[(3aS,4R,7S,7aS)-7-hydroxy-2,2,7-trimethyl-4,7a-dihydro-3aH-1,3-benzodioxol-4-yl]acetamide
• CAS: 1229922-63-7
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: YACVSEOKCJWMPL-WDCWCFNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-methylcyclohex-4-ene-1,2,3-triol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到(3aR,4S,5R,7aR)-2,6-dimethyl-4,5-O-isopropylidene-3a,4,5,7a-tetrahydrobenzo[d]oxazole-4,5-diol
  参考文献：
  名称：

  Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines

  摘要：

  Conjugated dienes were converted to 1,2-oxazines by reaction with an acyl nitroso dienophile. The oxazines were reduced to 1,4-N-acetylamino alcohols, which were rearranged to the corresponding oxazolines upon treatment with methanesulfonyl chloride or anhydride. The oxazolines yielded 1,2-N-acetylamino alcohols upon hydrolysis. Thus either 1,4- or 1,2-N-acetylamino alcohols are available from 1,3-dienes via this methodology. Experimental and spectral data are provided for all new compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.059
• 作为产物：
  描述：

  3-acetyl-1-methyl-5,6-O-isopropylidene-2-oxa-3-azabicyclo[2.2.2]oct-7-ene-5,6-diol 在 水 、 molybdenum hexacarbonyl 作用下， 以 乙腈 为溶剂， 以68%的产率得到(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-methylcyclohex-4-ene-1,2,3-triol
  参考文献：
  名称：

  Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines

  摘要：

  Conjugated dienes were converted to 1,2-oxazines by reaction with an acyl nitroso dienophile. The oxazines were reduced to 1,4-N-acetylamino alcohols, which were rearranged to the corresponding oxazolines upon treatment with methanesulfonyl chloride or anhydride. The oxazolines yielded 1,2-N-acetylamino alcohols upon hydrolysis. Thus either 1,4- or 1,2-N-acetylamino alcohols are available from 1,3-dienes via this methodology. Experimental and spectral data are provided for all new compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.059

文献信息

• PROCESS AND COMPOUNDS FOR THE MANUFACTURE OF OSELTAMIVIR AND ANALOGS THEREOF, AND NEW ANTIVIRAL AGENTS
  申请人：Hudlicky Tomas

  公开号：US20120252890A1

  公开（公告）日：2012-10-04

  The present application relates to processes for the preparation of intermediates useful in the manufacture of oseltamivir and the H 3 PO 4 salt of oseltamivir, Tamiflu®. The application further relates to novel intermediate and compounds and oseltamivir analogs and to pharmaceutical compositions comprising said analog compounds. The application further relates to a method of using the novel analogs of oseltamivir to treat or prevent influenza.

  本申请涉及用于制造奥司他韦和奥司他韦的H3PO4盐的中间体的制备过程。该申请还涉及新型中间体和化合物以及奥司他韦类似物和包含该类似物化合物的制药组合物。该申请还涉及使用新型奥司他韦类似物治疗或预防流感的方法。
• USE OF NEU1 SIALIDASE INHIBITORS IN THE TREATMENT OF CANCER
  申请人：Josefowitz Paul Zachary

  公开号：US20150064282A1

  公开（公告）日：2015-03-05

  Use of Neul sialidase inhibitors for the treatment of cancer as a monotherapy or in combination with known chemotherapeutics. Preferably, Neul sialidase inhibitors are oseltamivir phosphate or 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (DANA) or analogues thereof.
• US8716333B2
  申请人：——

  公开号：US8716333B2

  公开（公告）日：2014-05-06
• Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines
  作者：Lukas Werner、Jason Reed Hudlicky、Martina Wernerova、Tomas Hudlicky

  DOI：10.1016/j.tet.2010.03.059

  日期：2010.5

  Conjugated dienes were converted to 1,2-oxazines by reaction with an acyl nitroso dienophile. The oxazines were reduced to 1,4-N-acetylamino alcohols, which were rearranged to the corresponding oxazolines upon treatment with methanesulfonyl chloride or anhydride. The oxazolines yielded 1,2-N-acetylamino alcohols upon hydrolysis. Thus either 1,4- or 1,2-N-acetylamino alcohols are available from 1,3-dienes via this methodology. Experimental and spectral data are provided for all new compounds. (C) 2010 Elsevier Ltd. All rights reserved.