(E)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-nitro-α-D-galacto-hept-6-eno-1,5-pyranose | 56707-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (E)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-nitro-α-D-galacto-hept-6-eno-1,5-pyranose
• 英文别名: (E)-6,7-dideoxy-1,2,3,4-di-O-isopropylidene-7-nitro-α-D-galacto-hept-6-enopyranose；6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-nitro-α-D-galacto-hept-1-enopyranose；(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-8-[(E)-2-nitroethenyl]-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 56707-70-1
• 化学式: C₁₃H₁₉NO₇
• 分子量: 301.296
• InChiKey: PDOCTJUENKPCLN-YEAYLFKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-nitro-α-D-galacto-hept-6-eno-1,5-pyranose 生成 2-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]prop-2-enenitrile
  参考文献：
  名称：

  TRONCHET, JEAN M. J.;ZERELLI, SAMI, J. CARBOHYDR. CHEM., 8,(1989) N, C. 217-232

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2：3,4-二-O-异亚丙基-α-D-半乳糖-己二醛-1,5-吡喃糖 在 sodium acetate 作用下， 生成 (E)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-7-nitro-α-D-galacto-hept-6-eno-1,5-pyranose
  参考文献：
  名称：

  Influence of the structure of the sugar moiety on the cytotoxic and antiviral properties of sugar electrophiles.

  摘要：

  已经制备了带有2-硝基乙烯、1-氰基乙烯、3-硝基色烯-2-基或4-氰基色烯-2-基的受阻糖。它们的细胞毒性和化疗特性取决于糖部分的结构。其中一些对多瘤病毒具有活性的化合物是新抗病毒药物开发的先导。

  DOI：

  10.1248/cpb.36.3722

文献信息

• Formaldehyde dimethylhydrazone: A new neutral reagent for nucleophilic hydroformylation and hydrocyanation
  作者：José-María Lassaletta、Rosario Fernández、Consolación Gasch、Juan Vázquez

  DOI：10.1016/0040-4020(96)00466-8

  日期：1996.7

  MMPP. Therefore, formaldehyde dimethylhydrazone behaves as a new neutral formyl anion and cyanide equivalent, introducing a functionalized carbon unit β to the nitro group of a nitroolefin. Good yields and high stereoselectivities were obtained in the addition of 1 to a nitroolefin group within sugar derivatives, and no epimerization was observed in the cleavage of the dimethylhydrazone group.

  易于获得的标题化合物无需碱或催化即可顺利地添加到硝基烯烃中，从而以高收率得到β-硝基二甲基hydr烷3。迈克尔加合物3已通过臭氧分解成功转化为β-硝基醛，并通过MMPP处理以优异的收率转化为β-腈。因此，甲醛二甲基hydr表现为新的中性甲酰基阴离子和氰化物当量，将官能化的碳单元β引入硝基烯烃的硝基。在糖衍生物内的硝基烯烃基团上加1得到良好的产率和高的立体选择性，并且在二甲基hydr基团的裂解中未观察到差向异构化。
• Diastereoselective Synthesis of Branched-Chain Cyanonitrosugar Derivatives by Michael Addition/MMPP Oxidation Using Formaldehyde SAMP- and RAMP-Hydrazones as New Chiral Cyanide Equivalents
  作者：Rosario Fernández、Consolación Gasch、Jose-María Lassaletta、José-Manuel LLera

  DOI：10.1055/s-1996-4257

  日期：1996.5

  The diastereoselective synthesis of sugar derived β-nitro nitriles through double asymmetric induction experiments involving Michael addition of formaldehyde SAMP- and RAMP-hydrazones [(S)-1 and (R)-1] to sugar nitroolefins 2 in excellent overall yields and high diastereoselective excesses is described. The absolute configuration of the RAMP-hydrazone 1,4-adduct 3c was determined by chemical correlation of its corresponding β-nitro nitrile 4c.

  本文介绍了通过双不对称诱导实验，将甲醛 SAMP- 和 RAMP- 肼[(S)-1 和 (R)-1]与糖硝基烯烃 2 迈克尔加成，非对映选择性地合成糖衍生的δ-硝基腈，总产率优异，非对映选择性过量率高。RAMP- hydrazone 1,4-adduct 3c 的绝对构型是通过其相应的 δ-硝基腈 4c 的化学相关性确定的。
• Regio- and stereoselective synthesis of 3- and 5-(C-glycosyl)-4-nitroisoxazolidines by nitrone–nitroalkene [3+2] cycloaddition reactions
  作者：Pastora Borrachero、Francisca Cabrera、Mª Jesús Diánez、Mª Dolores Estrada、Manuel Gómez-Guillén、Amparo López-Castro、José Mª Moreno、José L. de Paz、Simeón Pérez-Garrido

  DOI：10.1016/s0957-4166(98)00488-1

  日期：1999.1

  Cycloaddition reactions of nitrones, including sugar nitrones, with nitroalkenes, including sugar nitroolefins, led with complete regioselectivity and stereospecificity to 4,5-trans-4-nitroisoxazolidines in 51-78% global yields. The endo/exo stereoselectivity depends on the type of sugar derivative used. As expected, the best pi-diastereofacial selectivity was observed when both partners were sugar derivatives. Isomerisation of the first formed diastereomers by the action of silica gel was observed in some cases. Absolute configurations for two crystalline products were assigned by X-ray diffraction methods. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 2-Glycosylchromene Derivatives
  作者：Jean M. J. Tronchet、Sami Zerelli、Gérald Bernardinelli

  DOI：10.1080/07328309908544000

  日期：1999.1.1

  Treated with salicylaldehyde or its 5-methoxy derivative, a series of blocked terminal (E)-nitroenoses undenwent a condensation reaction leading in fair to good yields to blocked 2-glycosyl-3-nitro-2H-chromene derivatives. Treated with cyanide, the nitro derivatives afforded 4-cyano-2-glycosyl-2H-chromenes via an addition-elimination reaction. These two types of chromenes bearing an electron-withdrawing group have been previously shown to have antiviral or cytotoxic properties related to their electrophilicity.