1,5-anhydro-D-tagatose | 172342-19-7

• 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: 1,5-anhydro-D-tagatose
• 英文别名: 1,5-anyhydro-D-tagatopyranose；(4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
• CAS: 172342-19-7
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: OCLOLUFOLJIQDC-PBXRRBTRSA-N

物化性质

• 沸点：
  405.0±45.0 °C(Predicted)
• 密度：
  1.521±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-D-tagatose 生成 (+/-)-epipentenomycin I
  参考文献：
  名称：

  BAUTE, MARIE-ANTOINETTE;DEFFIEUX, GERARD;BAUTE, ROBERT;BADOC, ALAIN;VERCA+, PHYTOCHEMISTRY, 30,(1991) N, C. 1419-1423

  摘要：

  DOI：
• 作为产物：
  描述：

  1,5-anhydro-3,4-O-isopropylidene-D-tagatopyranose 在 溶剂黄146 作用下， 反应 2.0h， 生成 1,5-anhydro-D-tagatose
  参考文献：
  名称：

  由D-半乳糖衍生物合成D-塔格糖和1,5-脱水-D-塔格糖。

  摘要：

  通过3,4,6-保护的D-吡喃半乳糖苷的氧化反应制得的3,4-O-异亚丙基-D-lyxo-己吡喃糖苷-2-ulose衍生物可以阴离子2,6-吡喃糖形式烷基化生成双-含2,5-二氧杂双环[2.2.2]辛烷环系统的糖苷。1-苄基-2-甲基双糖苷4b在进行催化氢解后，生成甲基D-lyxo-己吡喃并-2-uloside 10，以1：5-吡喃糖异构体9：8的混合物形式存在。计算并提供了NMR证据，以支持主要端基异构体具有α构型的假设。用NaBH4还原9/10可得到甲基3,4-O-异亚丙基-β-D-塔格吡喃糖苷，可以水解为D-塔格糖。还介绍了从1,5-脱水D-半乳糖醇开始的1,5-脱水D-塔格糖的简单合成。

  DOI：

  10.1016/0008-6215(95)00125-d

文献信息

• A convenient access to the 1,5-anhydro forms of d-tagatose, l-rhamnulose and d-xylulose via 2-hydroxyglycal esters
  作者：Pan Jarglis、Volker Göckel、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2009.03.016

  日期：2009.5

  Zemplen methanolysis or a three-step protocol comprising hydroxylaminolysis, de-O-acetylation and deoximination smoothly and efficiently convert the benzoylated 2-hydroxy-D-glycals Of D-galactose, L-rhamnose and D-Xylose into their configurationally related 1,5-anhydro-ketoses, thereby providing convenient access to the 1,5-anhydro forms of D-tagatose, L-rhamnulose and D-Xylulose. Invariably obtained as amorphous solids, they are best characterized through their highly crystalline oximes. (C) 2009 Elsevier Ltd. All rights reserved.
• Dimeric structures of 1,5-anhydro-d-fructose1Presented in part at the XVIIth International Carbohydrate Symposium, Milano, Italy, 1996, Abstract BP085.1
  作者：Stefan Freimund、Sabine Köpper

  DOI：10.1016/s0008-6215(98)00058-5

  日期：1998.3

  Upon treatment with acetic anhydride-pyridine, 1,5-anhydro-D-fructose gave the enolone 1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranose-2-ulose as a product of elimination, which is thus available in an overall yield of 25% from D-glucose. During this reaction, acetylated dimers of 1,5-anhydro-D-fructose were formed in a side reaction, whereas these were the only products when acidic acetylation conditions were applied. The acetylated dimers were isolated and served for an unequivocal structural assignment of dimeric forms of 1,5-anhydro-D-fructose 1 by NOESY experiments. Whereas anhydroketose 1 forms dimers in Me2SO and pyridine, its C-4 epimer, 1,5-anhydro-D-tagatose, did not form dimeric structures, neither in non aqueous nor in aqueous solvents. (C) 1998 Elsevier Science Ltd. All rights reserved.
• BAUTE, MARIE-ANTOINETTE;DEFFIEUX, GERARD;BAUTE, ROBERT;BADOC, ALAIN;VERCA+, PHYTOCHEMISTRY, 30,(1991) N, C. 1419-1423
  作者：BAUTE, MARIE-ANTOINETTE、DEFFIEUX, GERARD、BAUTE, ROBERT、BADOC, ALAIN、VERCA+

  DOI：——

  日期：——
• [EN] 1,5 AND 1,4-ANHYDROKETOSES, METHODS FOR THE PREPARATION OF 1,5-AND 1,4-ANHYDROKETOSES, INTERMEDIATES, AND USES OF 1,5-AND 1,4-ANHYDROKETOSES<br/>[FR] 1,5- ET 1,4-ANHYDROCETOSES, PROCEDES DE PREPARATION DE 1,5- ET 1,4-ANHYDROCETOSES, INTERMEDIAIRES, ET UTILISATIONS DE 1,5- ET 1,4-ANHYDROCETOSES
  申请人：GLYCOM APS

  公开号：WO2005121114A2

  公开（公告）日：2005-12-22

  The present invention relates to 1,4- and 1,5-anhydro-D-ketoses (monosaccharides, oligosaccharides and various glycoconjugates), e.g. 1,5-anhydro-D-fructose. Moreover, the invention provides synthetic methods and novel intermediates and precursors suitable for their preparation. The methods include catalytic- and/or pyrolitic sulfenic acid elimination of corresponding ß-hydroxy sulfoxides, N-deprotection of N-substituted-aminoglycals, O-deprotection of carbohydrate enolethers and/or O-acyl-substituted carbohydrate enols, and regio- and stereoselective modification and subsequent chemical transformation of bicyclic and/or tricyclic 1,4- and 1,5-anhydro-glycoderivatives. Furthermore, the present invention provides novel applications of 1,4- and 1,5-anhydroketoses within pharmaceutical, food and cosmetic industries.
• New syntheses of d-tagatose and of 1,5-anhydro-d-tagatose from d-galactose derivatives
  作者：Pier Luigi Barili、Giancarlo Berti、Giorgio Catelani、Felicia D'Andrea、Lucia Miarelli

  DOI：10.1016/0008-6215(95)00125-d

  日期：1995.9

  3,4-O-Isopropylidene-D-lyxo-hexopyranosid-2-ulose derivatives, obtained by oxidation of 3,4,6-protected D-galactopyranosides, can be alkylated in their anionic 2,6-pyranose forms to produce bis-glycosides containing the 2,5-dioxabicyclo[2.2.2]octane ring system. The 1-benzyl-2-methyl bis-glycoside 4b, when subjected to catalytic hydrogenolysis, produces the methyl D-lyxo-hexopyranos-2-uloside 10, existing

  通过3,4,6-保护的D-吡喃半乳糖苷的氧化反应制得的3,4-O-异亚丙基-D-lyxo-己吡喃糖苷-2-ulose衍生物可以阴离子2,6-吡喃糖形式烷基化生成双-含2,5-二氧杂双环[2.2.2]辛烷环系统的糖苷。1-苄基-2-甲基双糖苷4b在进行催化氢解后，生成甲基D-lyxo-己吡喃并-2-uloside 10，以1：5-吡喃糖异构体9：8的混合物形式存在。计算并提供了NMR证据，以支持主要端基异构体具有α构型的假设。用NaBH4还原9/10可得到甲基3,4-O-异亚丙基-β-D-塔格吡喃糖苷，可以水解为D-塔格糖。还介绍了从1,5-脱水D-半乳糖醇开始的1,5-脱水D-塔格糖的简单合成。