methyl α-D-lyxo-hexopyranosid-4-ulose | 102823-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl α-D-lyxo-hexopyranosid-4-ulose
• 英文别名: (2R,4R,5S,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-one
• CAS: 102823-45-0
• 化学式: C₇H₁₂O₆
• 分子量: 192.169
• InChiKey: PXYUEYYQRRNNRU-DAXDWZTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl α-D-lyxo-hexopyranosid-4-ulose 在 sodium tetrahydroborate 、 3 A molecular sieve 、 溴 、 三丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 4.13h， 生成 methyl α-D-arabino-hexopyranosid-2-ulose
  参考文献：
  名称：

  Tsuda, Yoshisuke; Hanajima, Makiko; Matsuhira, Naohisa, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 9, p. 2344 - 2350

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,4S,6R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one 在 溶剂黄146 作用下， 反应 0.67h， 以86%的产率得到methyl α-D-lyxo-hexopyranosid-4-ulose
  参考文献：
  名称：

  Utilization of Sugars in Organic Synthesis; Part XXVII. Chemistry of Oxo-Sugars. (2). Regio- and Stereo-Selective Synthesis of Methyl D-Hexopyranosiduloses and Identification of Their Forms Existing in Solutions.

  摘要：

  通过双二丁基氧化锡-溴法直接氧化未受保护的甲基糖苷，或先氧化受部分保护的糖苷再进行脱保护，选择性地合成了十六种具有不同区域和立体化学结构的甲基 D-吡喃己苷的氧化衍生物。通过 13C-NMR 光谱法研究了这些氧化糖苷在 Pryidine-d5 和 H2O（D2O）中的存在形式，发现氧化糖苷的氧化形式和水合物形式之间很容易发生相互转化。

  DOI：

  10.1248/cpb.41.491

文献信息

• Regioselective mono-oxidation of non-protected glycosides by the bis-tributyltin oxide-bromine method.
  作者：Yoshisuke Tsuda、Naohisa Matsuhira、Kimihiro (Yoshimoto) Kanemitsu

  DOI：10.1248/cpb.33.4095

  日期：——

  Treatment of methyl glycosides with an excess of bis-tributyltin oxide and molecular sieves 3A in chloroform followed by brominolysis resulted in monooxidation to yield oxo-glycosides regioselectively. Thus Me β-D-Glc and Me β-D-Xyl gave the 3-oxo derivatives in more than 90% yield, and Me α-D-Glc, Me α-D-Gal, Me α-D-Xyl, and Me β-L-Ara gave the 4-oxo derivatives in 70-80% yield.

  甲基糖苷与过量的二三丁基锡氧化物和分子筛3A在氯仿中反应，随后进行溴解反应，可以区域选择性地单氧化生成氧代糖苷。因此，Me β-D-葡糖苷和Me β-D-木糖苷以超过90%的产率得到3-氧代衍生物，而Me α-D-葡糖苷、Me α-D-半乳糖苷、Me α-D-木糖苷和Me β-L-阿拉伯糖苷以70-80%的产率得到4-氧代衍生物。
• Liu, Hong-Min; Tsuda, Yoshisuke, Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 1, p. 88 - 90
  作者：Liu, Hong-Min、Tsuda, Yoshisuke

  DOI：——

  日期：——
• TSUDA, YOSHISUKE;HANAJIMA, MAKIKO;MATSUHIRA, NAOHISA;OKUNO, YUKIHIRO;KANE+, CHEM. AND PHARM. BULL., 37,(1989) N, C. 2344-2350
  作者：TSUDA, YOSHISUKE、HANAJIMA, MAKIKO、MATSUHIRA, NAOHISA、OKUNO, YUKIHIRO、KANE+

  DOI：——

  日期：——
• Tsuda, Yoshisuke; Hanajima, Makiko; Matsuhira, Naohisa, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 9, p. 2344 - 2350
  作者：Tsuda, Yoshisuke、Hanajima, Makiko、Matsuhira, Naohisa、Okuno, Yukihiro、Kanemitsu, Kimihiro

  DOI：——

  日期：——
• Utilization of Sugars in Organic Synthesis; Part XXVII. Chemistry of Oxo-Sugars. (2). Regio- and Stereo-Selective Synthesis of Methyl D-Hexopyranosiduloses and Identification of Their Forms Existing in Solutions.
  作者：Hong-Min LIU、Yoshiyuki SATO、Yoshisuke TSUDA

  DOI：10.1248/cpb.41.491

  日期：——

  Sixteen oxo derivatives of methyl D-hexopyranosides with various regio- and stereo-chemistries were selectively synthesized by direct oxidation of non-protected methyl glycosides by the bistributyltin oxide-bromine method or by oxidation of pfrtially protected glycosides followed by deprotection. The forms of these oxoglycosides existing in pryidine-d5 and in H2O (D2O) were investigated by means of 13C-NMR spectroscopy, and it was found that interconversion between oxo and hydrate forms of oxoglycosides readily takes place.

  通过双二丁基氧化锡-溴法直接氧化未受保护的甲基糖苷，或先氧化受部分保护的糖苷再进行脱保护，选择性地合成了十六种具有不同区域和立体化学结构的甲基 D-吡喃己苷的氧化衍生物。通过 13C-NMR 光谱法研究了这些氧化糖苷在 Pryidine-d5 和 H2O（D2O）中的存在形式，发现氧化糖苷的氧化形式和水合物形式之间很容易发生相互转化。