(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-nitroethan-1-ol | 31281-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-nitroethan-1-ol
• 英文别名: (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-nitroethanol；1-(4R-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-nitroethanol；(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-nitroethanol
• CAS: 31281-69-3
• 化学式: C₇H₁₃NO₅
• 分子量: 191.184
• InChiKey: NUMMXFZHBMAYKM-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 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：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-nitroethan-1-ol 在 异氰酸苯酯 、 三乙胺 作用下， 生成 (S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(1-methoxy-cyclohexyloxy)-acetonitrile N-oxide
  参考文献：
  名称：

  检查手性腈氧化物与非手性烯烃反应中非面部选择的程度：通往β-羟基羧酸的途径

  摘要：

  已经开发了一种新的旋光性β-羟基羧酸的合成方法，该方法基于将手性腈氧化物（4）（适度）非对映选择性加成到1,2-二取代的烯烃上。

  DOI：

  10.1039/c39830001460
• 作为产物：
  描述：

  溴代硝基甲烷 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以62%的产率得到
  参考文献：
  名称：

  Synthesis of Sugar-Derived 2-Nitroalkanols via Henry Reaction Promoted by Samarium Diiodide or Indium

  摘要：

  We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI2 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI2-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes.

  DOI：

  10.1055/s-0031-1290441

文献信息

• Preliminary Studies on the Transformation of Nitrosugars into Branched Chain Iminosugars:  Synthesis of 1,4-Dideoxy-4-<i>C</i>-hydroxymethyl- 1,4-imino-pentanols
  作者：José M. Otero、Raquel G. Soengas、Juan C. Estévez、Ramón J. Estévez、David J. Watkin、Emma L. Evinson、Robert J. Nash、George W. J. Fleet

  DOI：10.1021/ol062887v

  日期：2007.2.1

  A novel promising strategy for the transformation of nitrosugars into branched pyrrolidines, based on double Henry reaction with formaldehyde followed by reductive ring closure, allowed the first enantiospecific synthesis of a 4-C-hydroxymethyl branched derivative of the well-known glycosidase inhibitor 1,4-dideoxy-1,4-imino-pentanol. This strategy also afforded a new route to some other interesting

  一种新的有前途的硝基糖转化为支链吡咯烷的新策略，该方法基于甲醛与甲醛的双重亨利反应，然后进行还原性闭环，从而实现了首个对映体特异性合成众所周知的糖苷酶抑制剂1,4的4-C-羟甲基支化衍生物。 -二脱氧-1，4-亚氨基戊醇。该策略还为寻找其他有趣的衍生物提供了新途径，例如N-羟基，N-丙氧基和亚氨基衍生物，这是一种具有良好生物学特性的新型化合物。[反应：请参见文字]。
• [EN] SYNTHESIS OF DESOSAMINES<br/>[FR] SYNTHÈSE DE DÉSOSAMINES
  申请人：HARVARD COLLEGE

  公开号：WO2016154533A1

  公开（公告）日：2016-09-29

  The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (Α') with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D') are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof.

  本发明提供了desosamine和mycaminose的类似物以及硝基糖和其制备方法。该发明还提供了将化合物（Α'）与乙二醛环化以给出公式（B）的硝基糖的方法。本发明还提供了制备公式（D'）化合物的方法，其中包括将硝基醇环化以给出硝基糖，并将硝基糖还原和烷基化以给出desosamine、mycaminose或其类似物的方法。
• Synthesis of <scp>D</scp> -Desosamine and Analogs by Rapid Assembly of 3-Amino Sugars
  作者：Ziyang Zhang、Takehiro Fukuzaki、Andrew G. Myers

  DOI：10.1002/anie.201507357

  日期：2016.1.11

  D‐Desosamine is synthesized in 4 steps from methyl vinyl ketone and sodium nitrite. The key step in this chromatography‐free synthesis is the coupling of (R)‐4‐nitro‐2‐butanol and glyoxal (trimeric form) mediated by cesium carbonate, which affords in crystalline form 3‐nitro‐3,4,6‐trideoxy‐α‐D‐glucose, a nitro sugar stereochemically homologous to D‐desosamine. This strategy has enabled the syntheses

  D-去糖胺是由甲基乙烯基酮和亚硝酸钠四步合成的。这种无色谱合成的关键步骤是碳酸铯介导的（R）-4-硝基-2-丁醇与乙二醛（三聚体形式）的偶联，其结晶形式为3-硝基-3,4,6- trideoxy-α- D-葡萄糖，一种与D-去糖胺立体化学同源的硝化糖。这种策略使合成一系列类似的3-硝基糖成为可能。在每种情况下，3-硝基糖都是通过结晶获得的纯净形式。
• A Study of the Influence of Base, Temperature and Reaction Time in Nitroaldol Reactions Using (R)-(+)-Glyceraldehyde Acetonide: Diastereoselective Synthesis of (4R, 5R)-Dihydro-5-((R)-1,2-Dihydroxyethyl)-4-Nitrofuran- 2(3H)-one
  作者：Erica Pennaforte、Jeronimo Costa、Cristiane Silva、Marcelo Saraiva、Vera Pereira

  DOI：10.2174/157017809787582771

  日期：2009.3.1

  The Henry reaction between the nitroalkanes 6-11 and (R)-(+)-glyceraldehyde acetonide (1), was investigated in respect to the variation of the base, temperature and reaction time. Nitroalcohols 5a-f were obtained in good yields (70- 85%) and moderate to good anti-selectivities (50-79%). The transformation of the nitroalcohol 5a,b in title γ-lactone 2, a potential precursor of bioactive β-aminoacids, was also investigated.

  研究了硝基烷烃 6-11 与(R)-(+)-甘油醛缩丙酮（1）之间的亨利反应在碱、温度和反应时间方面的变化。得到的硝基醇 5a-f 产率良好（70-85%），反选择性中等至良好（50-79%）。此外，还研究了硝基醇 5a,b 向标题 γ-内酯 2（一种具有生物活性的 β-氨基酸的潜在前体）的转化。
• Synthesis of desosamines
  申请人：President and Fellows of Harvard College

  公开号：US10544182B2

  公开（公告）日：2020-01-28

  The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (A′) with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D′) are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof.

  本发明提供脱糖胺和霉菌胺糖类似物和硝基糖及其制备方法。本发明还提供了式(A′)化合物与乙二醛环化得到式(B)硝基糖的方法。本发明提供了制备式(D′)化合物的方法，包括硝基醇环化得到硝基糖，硝基糖还原和烷基化得到脱糖胺、霉菌胺糖或其类似物。