(4S,4'R,5R)-2,2,2',2'-tetramethyl-5-((E)-2-nitrovinyl)-4,4'-bi(1,3-dioxolane) | 110220-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,4'R,5R)-2,2,2',2'-tetramethyl-5-((E)-2-nitrovinyl)-4,4'-bi(1,3-dioxolane)
• 英文别名: 3,4:5,6-Di-O-isopropyliden-D-arabino-1-nitro-1-hexen；(4S,5R)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5-[(E)-2-nitroethenyl]-1,3-dioxolane
• CAS: 110220-96-7
• 化学式: C₁₂H₁₉NO₆
• 分子量: 273.286
• InChiKey: OIAQSMIKWIQVDX-XUPSJDPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,4'R,5R)-2,2,2',2'-tetramethyl-5-((E)-2-nitrovinyl)-4,4'-bi(1,3-dioxolane) 生成 2-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-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：

  2,3-二氟-6-硝基苯胺 在 sodium acetate 作用下， 生成 (4S,4'R,5R)-2,2,2',2'-tetramethyl-5-((E)-2-nitrovinyl)-4,4'-bi(1,3-dioxolane)
  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

• Full acetals of β-d-glycopyranosylnitromethanes and a 1,2-dideoxy-1-nitroalk-1-enitol derived from common hexoses
  作者：Duy-Phong Pham-Huu、Mária Petrušová、James N. BeMiller、Peter Köll、Jüngen Kopf、Ladislav Petruš

  DOI：10.1016/s0008-6215(97)00203-6

  日期：1998.1

  Mono-O-benzylidenation of the starting compounds with benzaldehyde dimethyl acetal followed by O-isopropylidenation led to 4,6-O-benzylidene-2,3-O-isopropylidene acetals having better solubilities in non-polar solvents than the di-O-isopropylidene acetals. Di-O-benzylidenation of β- d -mannopyranosylnitromethane gave both (endo-2,3):4,6- and (exo-2,3):4,6-di-O-benzylidene acetals. Transacetalation of 1-deoxy-1-nitro-

  摘要在1,2中，由d-葡萄糖，d-半乳糖和d-甘露糖衍生的2,6-脱水-1-脱氧1-硝基醛糖（β-d-甘露糖基硝基甲烷）进行动力学控制的O-异丙基亚氨化。用4-甲苯磺酸催化的-二甲氧基乙烷得到高产率的2,3; 4,6-二-O-异亚丙基乙缩醛。对于d-甘露糖，还通过与2，2-二甲氧基丙烷反应以定量收率获得了双缩醛。起始化合物先与苯甲醛二甲基乙缩醛单-O-苄基化，然后再进行O-异亚丙基化，得到的4,6-O-亚苄基-2,3-O-异亚丙基缩醛在非极性溶剂中的溶解度高于二-O-异亚丙基乙缩醛。β-d-甘露吡喃糖基硝基甲烷的二-O-亚苄基化得到（endo-2,3）：4,6-和（exo-2,3）：4,6-di-O-亚苄基乙缩醛。
• Reaction of 1,2-anhydro-3,4:5,6-di-O-isopropylidene-1-C-nitro-d-mannitol with potassium hydrogenfluoride in ethylene glycol: a synthesis of 2-deoxy-2-fluoro-d-glucose
  作者：Walter A. Szarek、George W. Hay、Bogdan Doboszewski、Milton M. Perlmutter

  DOI：10.1016/s0008-6215(00)90137-x

  日期：1986.11

  The reaction of 1,2-anhydro-3,4:5,6-di-O-isopropylidene-1-C-nitro-d-mannitol (2) with potassium hydrogenfluoride in ethylene glycol under anhydrous conditions provides a route to 2-deoxy-2-fluoro-d-glucose, the 18F-labeled analog of which is an important radiopharmaceutical of use in medical imaging. The reaction is accompanied to a minor extent by epimerization at C-2 of the initially formed fluoro

  1,2-脱水-3,4：5,6-二-O-异亚丙基-1-C-硝基-d-甘露醇（2）与乙二醇中的氟化氢钾在无水条件下的反应为生成2-脱氧-2-氟-d-葡萄糖，其18F标记的类似物是用于医学成像的重要放射性药物。该反应在较小程度上伴随着最初形成的氟醛在C-2处的差向异构化，并且还会导致溶剂在C-2中发生攻击。
• Synthesis of isofagomine and some new azasugars as glycosidase inhibitors from d-mannitol derived nitroolefins
  作者：Rashmi Roy、Pavan K. Kancharla、Y. Suman Reddy、Anita Brar、Y.D. Vankar

  DOI：10.1016/j.tetasy.2013.09.021

  日期：2013.12

  The synthesis of isofagomine, epi-isofagomine and isofagomine analogues along with some new azasugars from two different vinyl nitro compounds, that were derived from D-mannitol, has been carried out. Two different synthetic strategies were followed for each of the vinyl-nitro precursors. Many of the azasugars synthesized showed inhibition in the micromolar range when tested against various glycosidase enzymes, opening up the possibility of modifying structural features for better and selective inhibition. (C) 2013 Elsevier 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.
• Formation of carbohydrate nitrocyclopropanes from nitroalditols
  作者：Bruno Radatus、Ursula Williams、Hans H. Baer

  DOI：10.1016/0008-6215(86)85072-8

  日期：1986.12