phenylmethyl-2,3-O-(1-methylethylidene)-β-D-gulofuranoside | 74912-02-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenylmethyl-2,3-O-(1-methylethylidene)-β-D-gulofuranoside
• 英文别名: (1R)-1-[(3aR,4R,6S,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]ethane-1,2-diol
• CAS: 74912-02-0
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: NKCNUNUEQRYLNZ-XLWJZTARSA-N

物化性质

• 沸点：
  468.8±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenylmethyl-2,3-O-(1-methylethylidene)-β-D-gulofuranoside 在 platinum on activated charcoal 盐酸 、 四氯化碳 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 草酰氯 、 氢气 、 双氧水 、 乙酸酐 、 lithium 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氨 、 乙酸乙酯 为溶剂， 反应 53.33h， 生成 (+/-)-methyl 8-epi nonactate
  参考文献：
  名称：

  Ireland, Robert E.; Vevert, Jean-Paul, Canadian Journal of Chemistry, 1981, vol. 59, p. 572 - 583

  摘要：

  DOI：
• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 硫酸 、 四丁基碘化铵 、 二异丁基氢化铝 、 copper(II) sulfate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 phenylmethyl-2,3-O-(1-methylethylidene)-β-D-gulofuranoside
  参考文献：
  名称：

  1-C-Alkyl imino-d-xylitol and -l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N-tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity

  摘要：

  The stereoselective synthesis of 1-C-alkyl iminosugars in the D-xylo and L-arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines generated using enantiopure tert-butanesulfinamide. Depending on the pentofuranose configuration and structure, the stereoselectivity of this reaction was found to be controlled either by the sugar moiety or by the stereogenic sulfur center. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.024

文献信息

• <scp>d</scp>-Gulonolactone as a Synthon for <scp>l</scp>-Noviose:  First Preparation of 4-<i>O</i>-Demethyl-<scp>l</scp>-noviofuranose and Related Derivatives
  作者：Marjan Ješelnik、Ivan Leban、Slovenko Polanc、Marijan Kočevar

  DOI：10.1021/ol034796t

  日期：2003.7.1

  D-Gulonolactone was initially converted in a few steps to the key ester derivative 7 [1-O-benzyl methyl 2,3-O-(1-methylethylidene)-alpha-L-lyxofuranosiduronate]. An appropriate selection of protecting groups enabled transformation of 7 under mild reaction conditions to 4-O-demethyl-L-noviofuranose 9a and related 9b-c. Derivatives 9 were further converted either to L-lyxopyranoses (10a and 10b) or to

  [反应：见正文]提出了新生物素的糖部分L-新葡聚糖（11）的新合成方法。D-古洛内酯最初在几个步骤中转化为关键酯衍生物7 [1-O-苄基甲基2,3-O-（1-甲基乙叉基）-α-L-呋喃呋喃二糖醛酸酯]。适当地选择保护基使得在温和的反应条件下7可以转化为4-O-脱甲基-L-新呋喃糖9a和相关的9b-c。衍生物9进一步转化为L-lyxopyranoses（10a和10b）或甲基L-lyx呋喃糖苷12。
• 1-C-Alkyl imino-d-xylitol and -l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N-tert-butanesulfinyl imines: sugar- versus chiral auxiliary-induced stereoselectivity
  作者：Farah Oulaïdi、Estelle Gallienne、Philippe Compain、Olivier R. Martin

  DOI：10.1016/j.tetasy.2011.02.024

  日期：2011.3

  The stereoselective synthesis of 1-C-alkyl iminosugars in the D-xylo and L-arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines generated using enantiopure tert-butanesulfinamide. Depending on the pentofuranose configuration and structure, the stereoselectivity of this reaction was found to be controlled either by the sugar moiety or by the stereogenic sulfur center. (C) 2011 Elsevier Ltd. All rights reserved.
• Ireland, Robert E.; Vevert, Jean-Paul, Canadian Journal of Chemistry, 1981, vol. 59, p. 572 - 583
  作者：Ireland, Robert E.、Vevert, Jean-Paul

  DOI：——

  日期：——