1,2;3,4-di-O-isopropylidene-6-trifluoromethanesulfonyl-α-D-tagatofuranose | 1015478-22-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1,2;3,4-di-O-isopropylidene-6-trifluoromethanesulfonyl-α-D-tagatofuranose
• 英文别名: 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulphonyl-D-tagatose；[(3'aS,4R,6'R,6'aS)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,4'-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole]-6'-yl]methyl trifluoromethanesulfonate
• CAS: 1015478-22-4
• 化学式: C₁₃H₁₉F₃O₈S
• 分子量: 392.35
• InChiKey: RFOSZJKJBYRDNP-JDVQERKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2;3,4-di-O-isopropylidene-6-trifluoromethanesulfonyl-α-D-tagatofuranose 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以88%的产率得到6-deoxy-1,2;3,4-di-O-isopropylidene-6-iodo-α-D-tagatofuranose
  参考文献：
  名称：

  酮呋喃糖苷的环外乙烯基醚

  摘要：

  糖的环外乙烯基醚衍生物存在于生物合成途径中，可以用作有用的合成中间体。糖的酮糖亚家族是该领域中特征最少的。因此，关于6- O离去基团的性质和4-羟基的保护，研究了通过β-消除法合成酮己糖的环外乙烯基醚衍生物。我们将该研究应用于4-羟基和6- O-离去基团处于顺式构型的受保护的l-山梨糖呋喃糖苷和d-塔古呋喃糖苷糖衍生物。还研究了一些反应，这些反应涉及塔格糖衍生的乙烯基醚产物的脱保护和还原性重排。

  DOI：

  10.1016/j.tet.2007.12.049
• 作为产物：
  描述：

  乳果糖杂质 在 吡啶 、 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 1,2;3,4-di-O-isopropylidene-6-trifluoromethanesulfonyl-α-D-tagatofuranose
  参考文献：
  名称：

  Looking-Glass Synergistic Pharmacological Chaperones: DGJ and L-DGJ from the Enantiomers of Tagatose

  摘要：

  The enantiomers of tagatose are converted to L-DGJ [a noncompetitive inhibitor of human lysosome alpha-galactosidase A (alpha-Gal A), K-i 38.5 mu M] and DGJ [a competitive inhibitor of alpha-Gal A, K-i 15.1 nM] in 66% yield. L-DGJ and DGJ provide the first examples of pharmacological chaperones that (a) are enantiomeric iminosugars and (b) have synergistic activity with implications for the treatment of lysosomal storage disorders and other protein deficiencies.

  DOI：

  10.1021/ol201552q

文献信息

• Exocyclic vinyl ethers of ketofuranosides
  作者：Yosi Bechor、Amnon Albeck

  DOI：10.1016/j.tet.2007.12.049

  日期：2008.2

  Exocyclic vinyl ether derivatives of sugars are found in biosynthetic pathways and may serve as useful synthetic intermediates. The ketose subfamily of sugars is the least characterized in this field. Thus, the synthesis of exocyclic vinyl ether derivatives of ketohexoses via β-elimination was studied with respect to the nature of the 6-O leaving group and the protection of the 4-hydroxy group. We

  糖的环外乙烯基醚衍生物存在于生物合成途径中，可以用作有用的合成中间体。糖的酮糖亚家族是该领域中特征最少的。因此，关于6- O离去基团的性质和4-羟基的保护，研究了通过β-消除法合成酮己糖的环外乙烯基醚衍生物。我们将该研究应用于4-羟基和6- O-离去基团处于顺式构型的受保护的l-山梨糖呋喃糖苷和d-塔古呋喃糖苷糖衍生物。还研究了一些反应，这些反应涉及塔格糖衍生的乙烯基醚产物的脱保护和还原性重排。
• Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-d-tagatose from l-fucose and of 6-deoxy-d-tagatose from d-fucose using Enterobacter agglomerans strain 221e
  作者：Akihide Yoshihara、Satoshi Haraguchi、Pushpakiran Gullapalli、Davendar Rao、Kenji Morimoto、Goro Takata、Nigel Jones、Sarah F. Jenkinson、Mark R. Wormald、Raymond A. Dwek、George W.J. Fleet、Ken Izumori

  DOI：10.1016/j.tetasy.2008.02.013

  日期：2008.4

  1-Deoxy-D-tagatose was produced by the hydrogenation of 6-deoxy-L-galactose (L-fucose) to L-fucitol followed by oxidation with Enterobacter agglomerans 221e; a similar sequence on D-fucose afforded 6-deoxy-D-tagatose. Thus, the polylol dehydrogenase recognizes the D-galacto-configuration of both D-fucitol and L-fucitol. The procedures were conducted in water and show the power of green, environmentally friendly biotechnology in the preparation of new monosaccharides with a potential for novel bioactive properties. 6-Deoxy-D-tagatose was also synthesized from D-tagatose via the efficient formation of 1,2:3,4-di-O-isopropylidene-alpha-D-tagatofuranose; a difficult final removal of protecting groups by acid makes the biotechnological route more attractive. (c) 2008 Elsevier Ltd. All rights reserved.
• Looking-Glass Synergistic Pharmacological Chaperones: DGJ and L-DGJ from the Enantiomers of Tagatose
  作者：Sarah F. Jenkinson、George W. J. Fleet、Robert J. Nash、Yuriko Koike、Isao Adachi、Akihide Yoshihara、Kenji Morimoto、Ken Izumori、Atsushi Kato

  DOI：10.1021/ol201552q

  日期：2011.8.5

  The enantiomers of tagatose are converted to L-DGJ [a noncompetitive inhibitor of human lysosome alpha-galactosidase A (alpha-Gal A), K-i 38.5 mu M] and DGJ [a competitive inhibitor of alpha-Gal A, K-i 15.1 nM] in 66% yield. L-DGJ and DGJ provide the first examples of pharmacological chaperones that (a) are enantiomeric iminosugars and (b) have synergistic activity with implications for the treatment of lysosomal storage disorders and other protein deficiencies.