3,6-anhydro-L-galactitol | 32742-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 3,6-anhydro-L-galactitol
• 英文别名: 1,4-Anhydro-d-galactitol；(2S,3R,4S)-2-[(1R)-1,2-dihydroxyethyl]oxolane-3,4-diol
• CAS: 32742-35-1
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: JNYAEWCLZODPBN-MOJAZDJTSA-N

物化性质

• 沸点：
  442.5±40.0 °C(Predicted)
• 密度：
  1.573±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-L-galactitol 在 硫酸 作用下， 生成 异山梨醇
  参考文献：
  名称：

  Biological upgrading of 3,6-anhydro-l-galactose from agarose to a new platform chemical

  摘要：

  这项研究展示了一种新型的生物升级技术（使用工程酵母细胞），将红色大型藻类生物质中主要但未被利用的糖——3,6-脱水-l-半乳糖升级为3,6-脱水-l-半乳醇，后者可转化为各种有价值的化学品，包括异山梨醇。

  DOI：

  10.1039/c9gc04265b
• 作为产物：
  描述：

  1,2,3,5,6-penta-O-acetyl-β-D-galactofuranose 在 盐酸 、 lithium aluminium tetrahydride 、 乙醚 、 溶剂黄146 作用下， 生成 3,6-anhydro-L-galactitol
  参考文献：
  名称：

  1,4-Anhydro-D-galactitol

  摘要：

  DOI：

  10.1021/ja01152a053

文献信息

• Intramolecular dehydration of biomass-derived sugar alcohols in high-temperature water
  作者：Aritomo Yamaguchi、Natsumi Muramatsu、Naoki Mimura、Masayuki Shirai、Osamu Sato

  DOI：10.1039/c6cp06831f

  日期：——

  The intramolecular dehydration of biomass-derived sugar alcohols D-sorbitol, D-mannitol, galactitol, xylitol, ribitol, L-arabitol, erythritol, L-threitol, and DL-threitol was investigated in high-temperature water at 523–573 K without the addition of any acid catalysts. D-Sorbitol and D-mannitol were dehydrated into isosorbide and isomannide, respectively, as dianhydrohexitol products. Galactitol was

  生物质衍生的糖醇的分子内脱水d -山梨醇，d -mannitol，半乳糖醇，木糖醇，核糖醇，大号-arabitol，赤藓醇，大号-threitol，和DL -threitol在523-573 K的高温水进行了研究，而不添加任何酸催化剂。将D-山梨糖醇和D-甘露糖醇分别脱水为异山梨醇和异甘露糖醇，作为二脱水己糖醇产物。将半乳糖脱水为脱水半乳糖；然而，由于C-3和C-6位羟基的取向，脱水半乳糖醇不能脱水成双脱水半乳糖产物。戊糖，例如木糖醇，核糖醇和L-阿拉伯糖醇脱水成脱水戊糖醇。含有在羟基的戊糖醇的脱水率的反式的形式，这在产品的四氢呋喃保持为羟基基团，比含羟基基团的那些更大的顺式形式，因为所引起的的羟基基团的结构阻碍的顺期间形式脱水过程。在四糖醇的情况下，赤藓糖醇的脱水比苏糖醇的脱水慢，这也可以通过羟基的结构障碍来解释。L-苏糖醇的脱水速度比DL快-苏糖醇，这意味着分子簇是由水中糖醇之间的氢键
• Production of carbohydrate building blocks from red seaweed polysaccharides. Efficient conversion of galactans into C-glycosyl aldehydes
  作者：Diogo R. B. Ducatti、Alessandro Massi、Miguel D. Noseda、Maria Eugênia R. Duarte、Alessandro Dondoni

  DOI：10.1039/b816606d

  日期：——

  and D-galactose, respectively) derivatives. Complete depolymerization of agarose and kappa-carrageenan under harsher conditions produced 3,6-anhydro L- and D-galactose aldehyde derivatives. Chain shortening of these products via alditol formation and oxidative carbon-carbon bond cleavage furnished C-formyl α-L- and α-D-threofuranosides. The above C-glycosyl aldehydes were all prepared on a meaningful

  琼脂和角叉菜胶是丰富的天然多糖，可通过以下方法大规模获得 水从各种红色海藻中提取。这些半乳聚糖，除了是制药和食品工业的有价值的产品外，还是低成本的原料，用于制备有用的和稀有的，基于碳水化合物的结构单元，这些单元很难通过全合成获得，而且价格昂贵。半合成L-和D-构象的两组C-糖基醛的半合成。琼脂糖分别描述了α-角叉菜胶和κ-角叉菜胶。简而言之，在温和条件下，两个半乳聚糖的部分酸催化巯基分解反应得到琼脂二糖 和角蛋白（β- d -Gal p - （1→4）-3,6-脱水-醛基-大号- 和 D-半乳糖）。完全解聚琼脂糖 和κ-角叉菜胶在更苛刻的条件下产生 3,6-脱水 L-和D-半乳糖醛衍生物。通过醛糖醇形成和氧化碳-碳键裂解提供的这些产品的链缩短C-甲酰基α- L-和α- D-呋喃呋喃糖苷。以上C-糖基醛均以克量的半乳聚糖为起始以有意义的制备规模制备。最终，通过Baeyer-Villiger氧化苄基化反应建立了一种新的制备2
• Sulfuric Acid-Catalyzed Dehydration of Sorbitol: Mechanistic Study on Preferential Formation of 1,4-Sorbitan
  作者：Mizuho Yabushita、Hirokazu Kobayashi、Abhijit Shrotri、Kenji Hara、Shogo Ito、Atsushi Fukuoka

  DOI：10.1246/bcsj.20150080

  日期：2015.7.15

  1,4-Sorbitan is a precursor to environmentally benign surfactants, which can be produced from biomass via sorbitol. Currently, sulfuric acid-catalyzed dehydration of sorbitol is the most widely used route for industrial synthesis of 1,4-sorbitan. In this work, we have studied the mechanism of the sorbitol dehydration by sulfuric acid. Our results show that both thermodynamic and kinetic parameters play significant roles to determine the yield of 1,4-sorbitan. Sorbitol preferentially forms an adduct with sulfuric acid, thereby inhibiting the subsequent dehydration of 1,4-sorbitan to isosorbide. Furthermore, a reaction mechanism is proposed for the dehydration reaction, which involves an SN2 reaction on primary C1 of sorbitol attacked by OH of secondary C4.

  1,4-山梨醇是一种环保型表面活性剂的前体，可通过山梨醇从生物质中生产。目前，硫酸催化山梨醇脱水是工业合成 1,4-山梨醇酐最广泛使用的途径。在这项工作中，我们研究了硫酸催化山梨醇脱水的机理。研究结果表明，热力学和动力学参数对 1,4-山梨糖醇的产率起着重要作用。山梨醇优先与硫酸形成加合物，从而抑制了 1,4-山梨醇随后脱水生成异山梨醇苷。此外，还提出了脱水反应的反应机理，即山梨醇的一级 C1 受二级 C4 的羟基攻击而发生 SN2 反应。
• Aqueous semisynthesis of <i>C</i>-glycoside glycamines from agarose
  作者：Juliana C Cunico Dallagnol、Alexandre Orsato、Diogo R B Ducatti、Miguel D Noseda、Maria Eugênia R Duarte、Alan G Gonçalves

  DOI：10.3762/bjoc.13.121

  日期：——

  Agarose was herein employed as starting material to produce primary, secondary and tertiary C-glycoside glycamines, including mono- and disaccharide structures. The semisynthetic approach utilized was generally based on polysaccharide-controlled hydrolysis followed by reductive amination. All reactions were conducted in aqueous media and without the need of hydroxyl group protection. We were able to

  琼脂糖在本文中用作产生伯，仲和叔C-糖苷甘胺，包括单糖和二糖结构的原料。所使用的半合成方法通常基于多糖控制的水解，然后进行还原胺化。所有反应均在水性介质中进行，不需要羟基保护。我们能够确定琼脂水解产物还原胺化的最佳条件，并克服与这种反应有关的主要困难，并将其扩展到还原脱水糖。过量的乙酸铵，甲胺或二甲胺以及使用稀释的碱性（pH 11）反应介质被认为是提高产量的重要方面，以及减少通常与碳水化合物还原胺化有关的副产物的量。该策略允许将3,6-脱水-α-L-吡喃半乳糖单元（天然存在于琼脂糖结构中）转移到所有合成的甘胺上，构成一个氨基取代的C-苏呋喃糖苷部分，与（+）密切相关-毒蕈碱。
• Kinetic analyses of intramolecular dehydration of hexitols in high-temperature water
  作者：Aritomo Yamaguchi、Naoki Mimura、Masayuki Shirai、Osamu Sato

  DOI：10.1016/j.carres.2019.107880

  日期：2020.1

  Intramolecular dehydration of the biomass-derived hexitols D-sorbitol, D-mannitol, and galactitol was investigated. These reactions were performed in high-temperature water at 523-573 K without added acid catalyst. The rate constants for the dehydration steps in the reaction networks were determined at various reaction temperatures, and the activation energies and pre-exponential factors were calculated from Arrhenius plots. The yield of each product was estimated as a function of reaction time and temperature using the calculated rate constants and activation energies. The maximum yield of each product from the dehydration reactions was predicted over a range of reaction time and temperature, allowing the selective production of these important platform chemicals.