methyl O⁴,O⁶-(R)-benzylidene-O²,O³-dimethyl-α-D-mannopyranoside | 53767-28-5

• 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 O⁴,O⁶-(R)-benzylidene-O²,O³-dimethyl-α-D-mannopyranoside
• 英文别名: (4aR,6S,7S,8S,8aR)-6,7,8-trimethoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 53767-28-5
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: ZOYHXXDGSUTGIY-AVBIWOEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl O⁴,O⁶-(R)-benzylidene-O²,O³-dimethyl-α-D-mannopyranoside 生成 Benzoic acid (2R,3R,4S,5S,6S)-2-hydroxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  SATO, KEN-ICHI;JGARASHI, TETSUTARO;YANAGISAWA, YUKIO;KAWAUCHI, NOBUYA;HAS+, CHEM. LETT.,(1988) N 10, C. 1699-1702

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 (4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-7,8-dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以9%的产率得到methyl O⁴,O⁶-(R)-benzylidene-O²,O³-dimethyl-α-D-mannopyranoside
  参考文献：
  名称：

  Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and ¹H, ¹³C, and ¹⁹F NMR Spectroscopic Investigation

  摘要：

  The title question is addressed by low-temperature H-1, C-13, and F-19 NMR spectroscopies in CD2Cl2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At -78 degrees C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at -78 degrees C in CD2Cl2 and allowed to warm gradually until decomposition was detected by H-1 and F-19 NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.

  DOI：

  10.1021/ja971239r

文献信息

• Synthesis of some methylated tetroses and pentoses
  作者：G. G. S. Dutton、K. B. Gibney、P. E. Reid

  DOI：10.1139/v69-411

  日期：1969.7.1

  Oxidation of 2,3-di-O-methyl-D-glucitol (≡ 4,5-di-O-methyl-L-gulitol) and 2,3-di-O-methyl-D-mannitol (≡ 4,5-di-O-methyl-D-mannitol) with an excess of periodate gave 2,3-di-O-methyl-L-threose and 2,3-di-O-methyl-D-erythrose, each characterized as the 2,4-dinitrophenylhydrazone. Borohydride reduction of the sugars gave 2,3-di-O-methyl-L-threitol and 2,3-di-O-methylerythritol characterized as their di-p-nitrobenzoates

  氧化 2,3-二-O-甲基-D-葡萄糖醇 (≡ 4,5-二-O-甲基-L-gulitol) 和 2,3-二-O-甲基-D-甘露糖醇 (≡ 4,5 -二-O-甲基-D-甘露糖醇）与过量的高碘酸盐得到 2,3-二-O-甲基-L-苏糖和 2,3-二-O-甲基-D-赤藓糖，每个表征为 2 ,4-二硝基苯腙。糖的硼氢化物还原得到 2,3-二-O-甲基-L-苏糖醇和 2,3-二-O-甲基赤藓糖醇，表征为它们的二-对-硝基苯甲酸酯。用 1 摩尔高碘酸盐氧化己糖醇得到 3,4-二-O-甲基-L-木糖，其特征为甲基 3,4-二-O-甲基-α-L-吡喃木糖苷和 3,4-二-O-甲基-D-阿拉伯糖被鉴定为3,4-二-O-甲基-D-阿拉伯酰胺。还制备了 2-O-甲基-D-赤藓糖醇（≡ 3-O-甲基-L-赤藓糖醇）和 1-O-甲基-D-苏糖醇（≡ 4-O-甲基-D-苏糖醇）并表征为三对硝基苯甲酸酯。
• Enantioselective alkylation of aldehydes using dialkylzincs catalyzed by simple chiral diols derived from naturally occurring monosaccharides
  作者：Kyosuke Michigami、Masahiko Hayashi

  DOI：10.1016/j.tet.2013.03.090

  日期：2013.5

  Enantioselective alkylation of aldehydes was achieved in up to 84% ee using dialkylzincs catalyzed by simple dials derived from naturally occurring monosaccharides. (C) 2013 Elsevier Ltd. All rights reserved.