3,6-di-O-acetyl-4-O-methyl-D-glucal | 34820-20-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,6-di-O-acetyl-4-O-methyl-D-glucal
• 英文别名: O³,O⁶-diacetyl-O⁴-methyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol；O³,O⁶-Diacetyl-O⁴-methyl-1,5-anhydro-2-desoxy-D-arabino-hex-1-enit；[(2R,3S,4R)-4-acetyloxy-3-methoxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 34820-20-7
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: GEVPJIBATYTYCJ-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-di-O-acetyl-4-O-methyl-D-glucal 在 solid phase supported Candida antarctica lipase B 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以86%的产率得到6-O-acetyl-4-O-methyl-D-glucal
  参考文献：
  名称：

  New chemo-enzymatic route toward N-acetylneuraminic acid derivatives with alkyl groups at C-7 hydroxyl group

  摘要：

  Based on chemo-enzymatic regio- and stereoselective reactions, new routes toward C-4 substituted N-acetyl-D-mannosamine (ManNAc) and the corresponding sialic acids from D-glucal were established. Lipase-catalyzed regioselective transformation of n-glucal and related substrates furnished precursors on which carbamate and alkyl substituent were properly introduced at C-3 and at C-4, respectively. Cyclic carbamate formation through rhodium-nitrenoid intermediates with iodobenzene pivalate and tertbutyl alcohol proceeded in manna-configured at C-2 as well as alpha- at C-1, exclusively. Ring opening and deprotection under mild conditions furnished the target ManNAc derivatives, which were the substrates for aldolase-catalyzed reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.045
• 作为产物：
  描述：

  1,6-anhydro-2,3-di-O-isopropylidene-4-O-methyl-β-D-mannopyranose 在 氢溴酸 、 溶剂黄146 、 锌 作用下， 生成 3,6-di-O-acetyl-4-O-methyl-D-glucal
  参考文献：
  名称：

  Eine weitere Synthese des 4-Methyl-2,3,6-triacetyl-?-d-methylglucosids

  摘要：

  DOI：

  10.1007/bf00905417

文献信息

• Electronic Factors in the<i>C</i>-Glycosidation with Silylacetylene
  作者：Minoru Isobe、Rungnapha Saeeng、Rena Nishizawa、Masato Konobe、Toshio Nishikawa

  DOI：10.1246/cl.1999.467

  日期：1999.6

  Two kinds of electronic factors have been clarified to control the reactivity in alkynylation of glycals with silylacetylenes. One is that the reactivity of nucleophile silylpropargyl alcohol derivative largely depends on the protecting group. The second factor is found in the similar electrophiles as oxocarbenium intermediates that were generated from glucals or galactals. Diminished reactivity was found with the 4-axial substituents such as acetoxy or methoxy group.

  两种电子因素已被明确，用于控制糖醛与硅乙炔的炔化反应。一是亲核硅丙炔醇衍生物的反应性很大程度上取决于保护基团。第二个因素存在于类似电离性中间体，这些中间体由糖醛或半乳糖醛生成。研究发现，4轴取代基（如乙酰氧基或甲氧基）的反应性降低。
• �ber 4-Methyl-glucurons�ure
  作者：A. Wacek、F. Leitinger、P. Hochbahn

  DOI：10.1007/bf00903021

  日期：——