3,5,6-trideoxy-1,2-O-isopropylidene-6-nitro-α-D-erythro-hex-5-enofuranose | 122799-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5,6-trideoxy-1,2-O-isopropylidene-6-nitro-α-D-erythro-hex-5-enofuranose
• 英文别名: 3,5-dideoxy-1,2-O-isopropylidene-5-nitromethylene-α-D-xylofuranose；3,5,6-trideoxy-1,2-O-isopropyIidene-6-nitro-α-D-erythro-hex-5-enofuranose
• CAS: 122799-46-6
• 化学式: C₉H₁₃NO₅
• 分子量: 215.206
• InChiKey: BQKQWLICGMRCQV-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  70.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,5,6-trideoxy-1,2-O-isopropylidene-6-nitro-α-D-erythro-hex-5-enofuranose 在 platinum(IV) oxide 吡啶 、 盐酸 、 sodium periodate 、 Amberlite IR-120 (H⁽¹⁺⁾) 、 氢气 、 sodium methylate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 36.5h， 生成 Methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-3-O-methyl-β-D-erythro-pentopyranoside
  参考文献：
  名称：

  Hanaya, Tadashi; Noguchi, Ayashi; Armour, Margaret-Ann, Journal of the Chemical Society. Perkin transactions I, 1992, # 2, p. 295 - 301

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-nitroethanol 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3,5,6-trideoxy-1,2-O-isopropylidene-6-nitro-α-D-erythro-hex-5-enofuranose
  参考文献：
  名称：

  Studies on the stereocontrolled transformation of nitrohexofuranoses into 2-oxabicyclo[2.2.1]heptanes. V: Synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate

  摘要：

  The first total synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on an intramolecular cyclisation leading to 2-oxabicyclo[2 2 1]heptane derivatives It was observed that on of the substrate anomers produces an elimination rather than a cyclisation reaction These and other differences in the reaction paths for this key step were rationalised by means of molecular mechanism based Calculations. (c) 2010 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetasy.2009.12.018

文献信息

• Synthesis of 2,4-Dideoxy-4-[(<i>S</i>)-methyl- and (<i>R</i>)-cyclohexylphosphinyl]-α,β-D-<i>erythro</i>-pentofuranoses. The First P-in-Ring Sugar Analogues of 2-Deoxy-D-ribofuranose Type
  作者：Hiroshi Yamamoto、Ayashi Noguchi、Kenji Torii、Keiji Ohno、Tadashi Hanaya、Heizan Kawamoto、Saburo Inokawa

  DOI：10.1246/cl.1988.1575

  日期：1988.9.5

  Starting with 3-deoxy-1,2-O-isopropylidene-α-d-ribo-hexofuranose, methyl 2,4-dideoxy-4-[(methoxy)methyl- and cyclohexylphosphinyl]-d-glycero-pentopyranosides were prepared in a 9 step sequence (20–25% overall yield). These were converted into the title compounds, which were characterized as the 1,3,5-tri-O-acetates.

  以3-脱氧-1,2-O-异亚丙基-α-d-呋喃核己糖为起始物，通过9步反应（总产率为20-25%）合成了甲基2,4-二脱氧-4-[(甲氧基)甲基-和环己基膦基]-d-甘露呋喃庚糖苷。这些产物被转化成标题化合物，并被鉴定为1,3,5-三-O-乙酸酯。
• WO2008/152386
  申请人：——

  公开号：——

  公开（公告）日：——
• An efficient synthesis of 2,4-dideoxy-4-hydroxyphosphinyl-d-erythro-pentofuranose
  作者：Tadashi Hanaya、Ayashi Noguchi、Hiroshi Yamamoto

  DOI：10.1016/0008-6215(91)80173-k

  日期：1991.1