methyl 6-O-methyl-α-D-galactopyranoside | 7045-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-methyl-α-D-galactopyranoside
• 英文别名: methyl O⁶-methyl-α-D-galactopyranoside；methyl-(O⁶-methyl-α-D-galactopyranoside)；Methyl-(O⁶-methyl-α-D-galactopyranosid)；(2S,3R,4S,5R,6R)-2-methoxy-6-(methoxymethyl)oxane-3,4,5-triol
• CAS: 7045-61-6
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: FJFRHMFVCLTWOW-HNEXDWKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-O-methyl-α-D-galactopyranoside 在 水 、 过碘酸 作用下， 生成 (R)-3-methoxy-2-((S)-1-methoxy-2-oxo-ethoxy)-propionaldehyde
  参考文献：
  名称：

  Reduction of the Products of Periodate Oxidation of Carbohydrates. IV. Hydrogenation with Palladium-Charcoal of the Dialdehydes from Methyl Glycosides^1,2

  摘要：

  DOI：

  10.1021/ja01560a051
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、506.62 kPa 条件下， 反应 36.0h， 生成 methyl 6-O-methyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084

文献信息

• Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid
  作者：Evgeny V. Evtushenko

  DOI：10.1016/s0008-6215(99)00044-0

  日期：1999.3

  Abstract Partial methylation of the methyl pyranosides of a number of pentoses, hexoses, 6-deoxyhexoses, methyl uronates and their methyl ethers with diazomethane in the presence of transition-metal chlorides and boric acid was studied. It was found for methyl glycosides of pentoses and 6-deoxyhexoses that tin(II), antimony(III), and titanium(IV) chlorides as well as boric acid promoted substitution

  摘要研究了在过渡金属氯化物和硼酸存在下，许多戊糖，己糖，6-脱氧己糖，尿酸甲酯及其甲基醚的甲基吡喃糖苷与重氮甲烷的部分甲基化。发现戊糖和6-脱氧己糖的甲基糖苷中锡（II），锑（III）和钛（IV）氯化物以及硼酸主要促进OH-3的取代，但被铈（III）和锌的取代（II）观察到盐主要取代了OH-2。在所有情况下，甲基β-1-鼠李糖吡喃糖苷的甲基化表现出较高的OH-2反应性。在氯化锡（II），锑（III）和铈（III）的存在下，己糖甲基糖苷的甲基化反应主要产生了3-甲基醚。不参与进一步络合的3-甲基醚 积聚高达50-80％的反应混合物（95％至100％的单甲醚馏分）。建议用于许多糖的方便的甲基醚的合成。
• Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)
  作者：Masao Shiozaki、Takuya Tashiro、Hiroyuki Koshino、Ryusuke Nakagawa、Sayo Inoue、Tomokuni Shigeura、Hiroshi Watarai、Masaru Taniguchi、Kenji Mori

  DOI：10.1016/j.carres.2010.05.003

  日期：2010.8

  (alphaGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in alphaGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNgamma

  α-半乳糖苷神经酰胺（alphaGalCer，KRN7000）由于具有结合CD1d分子介导的iNKT细胞的能力，已被鉴定为免疫过程的调节剂。从d-阿拉伯糖醇或l-核糖合成了alphaGalCer中的酰胺基被酯或醚基取代时的一些类似物，以评估其激活iNKT细胞的能力。酯类似物30a，31a和61显示出对iNKT细胞产生IFNγ和IL-4的活性，而α-半乳糖基神经酰胺的醚（31b）和4-甲氧基酯（76）类似物对iNKT细胞没有活性。
• Methylation Studies on Dialdehydes Obtained from Methyl Glycosides by Periodate Oxidation¹
  作者：Irwin J. Goldstein、F. Smith

  DOI：10.1021/ja01498a046

  日期：1960.7
• A convenient method for the preparation of all of the partially methylated derivatives of methyl α-d-mannopyranoside and α-d-galactopyranoside
  作者：Tomohiro Mega、Atsushi Nishikawa、Tokuji Ikenaka

  DOI：10.1016/0008-6215(83)88296-2

  日期：1983.2
• Synthesis of D- and of L-α-O-Methylglycerol¹
  作者：Irwin J. Goldstein、J. K. Hamilton、F. Smith

  DOI：10.1021/ja01562a043

  日期：1957.3