methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside | 66008-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,4aR,6S,8aS)-6-methoxy-8-nitro-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine
• CAS: 66008-34-2
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: LUKNPLGKZJKOPN-ZOBORPQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside 在 乙酸酐 作用下， 反应 4.0h， 生成 3-((4S)-5t-acetoxy-2c-phenyl-[1,3]dioxan-4r-yl)-5-benzoyl-isoxazole-4-carbaldehyde
  参考文献：
  名称：

  硝基糖与苯甲锍制备异恶唑衍生物

  摘要：

  甲基 4,6-O-benzylidene-2,3-dideoxy-3-nitro-α-D-erythro-hex-2-enopyranoside 或 5-benzoyl (methyl 4,6-O-benzylidene-2,3 -dideoxy-α-D-erythro-hexopyranosido)[3,2-c]isoxazoline N-oxide 与二甲基锍 phenacylide 生成 5-benzoyl-3-(1,3-O-benzylidene-D-erythro-glyceryl)-4-异恶唑甲醛收率相当好。

  DOI：

  10.1246/bcsj.51.3401
• 作为产物：
  描述：

  (2R,4aR,6S,8R,8aS)-6-Methoxy-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以95%的产率得到methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Synthesis of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-formyl-α-d-erythro-hex-2-enopyranoside

  摘要：

  The synthesis of the title compound was achieved in seven steps and 61 % overall yield from methyl alpha-D-glucopyranoside. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.018

文献信息

• Preparation of isoxazoline N-oxide derivatives from a nitro-sugar and S-ylides
  作者：Tohru Sakakibara、Rokuro Sudoh

  DOI：10.1039/c39770000007

  日期：——

  Axial attack predominates over equatorial attack in the addition of dimethylsulphoxonium methylide and ethyl dimethylsulphuranylideneacetate to the nitro-sugar (1); axial attack selectively gave the 1,4-addition products (3) and (6), whereas equatorial attack afforded the 1,2-addition products (2) and (4), respectively.

  在硝化糖中添加二甲基亚砜基亚砜和乙基二甲基亚磺酰亚砜基乙酸酯，在轴向侵蚀方面比赤道侵蚀更重要（1）；轴向侵蚀选择性地给出了1,4加成产物（3）和（6），而赤道侵蚀分别给出了1,2加成产物（2）和（4）。
• Photoaddition reactions of 3-nitro-2-enopyranoside derivatives in 1,3-dioxolane
  作者：Tohru Sakakibara、Aya Takaide、Akinori Seta

  DOI：10.1016/0008-6215(92)84075-4

  日期：1992.3

  Abstract Irradiation of 3-nitro-2-enopyranoside derivatives having α- d -erythro, β- d -hreo, and α- d -threo configurations in 1,3-dioxolane afforded adducts in moderate yields. Structural assignment of the adducts, including conformational analyses of the 1,3-dioxolanyl moiety, were performed.

  摘要在1，3-二氧戊环中辐射具有α-d-赤型，β-d-hreo和α-d-苏型构型的3-硝基-2-烯吡喃糖苷衍生物可得到中等收率的加合物。进行了加合物的结构分配，包括1,3-二氧戊环基部分的构象分析。
• Preparation of a methyl 3,4-dideoxy-3-C-nitro-α-d-threo-hex-3-enopyranoside bearing a peroxy function at C-2 and its reactions with some nucleophiles
  作者：Akinori Seta、Kiohisa Tokuda、Tohru Sakakibara

  DOI：10.1016/0008-6215(94)00318-a

  日期：1995.3

  Abstract Treatment of 4,6-diacetate 3 with tert -butyl hydroperoxide gave the S N 2′ product 6 in high yield, the formation of which presumeably involves an intermediary nitronate. The thus prepared 6 reacted with nucleophiles to afford 2,3-anhydro derivatives having the talo configuration.

  摘要用叔丁基氢过氧化物处理4,6-二乙酸酯3可得到高收率的SN 2'产物6，其形成可能涉及中间体亚硝酸盐。如此制备的6与亲核试剂反应，得到具有talo构型的2，3-脱水衍生物。
• Experimental and theoretical study of a Diels–Alder reaction between a sugar-derived nitroalkene and cyclopentadiene
  作者：María I. Mangione、Ariel M. Sarotti、Alejandra G. Suárez、Rolando A. Spanevello

  DOI：10.1016/j.carres.2010.12.006

  日期：2011.3

  The Diels-Alder reaction of a pyranose-derived nitroalkene 1 with cyclopentadiene is described, and the unexpected facial selectivity of the cycloaddition is analyzed by a computational study.

  描述了吡喃糖衍生的硝基烯烃1与环戊二烯的Diels-Alder反应，并通过计算研究分析了环加成反应的出乎意料的面部选择性。
• Experimental and Theoretical (AM1) Studies on Photoaddition Reactions of 3-Nitro-2-enopyranoside Derivatives.
  作者：Tohru Sakakibara、Ichiro Matuo、Aya Takaide、Takanori Nakamura、Akinori Seta

  DOI：10.1246/cl.1992.177

  日期：——

  3-nitro-α- and β-D-erythro-hex-2-enopyranoside derivatives in methanol, ethanol, and isopropanol with high pressure Hg lamp gave the adducts in moderate yields. The stereoselectivities calculated by AM1 calculation by the use of model compounds with 1,3-dioxolan-2-yl radical are not conflict with those observed in similar photoreaction in 1,3-dioxolane as well as the present results

  用高压汞灯照射甲醇、乙醇和异丙醇中的 3-硝基-α-和 β-D-erythro-hex-2-enopyranoside 衍生物，得到中等产率的加合物。使用具有 1,3-dioxolan-2-yl 自由基的模型化合物通过 AM1 计算计算的立体选择性与在 1,3-dioxolane 中类似光反应中观察到的立体选择性以及目前的结果没有冲突