L-Arabinitol, 2,3,4-tri-O-methyl- | 14550-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-Arabinitol, 2,3,4-tri-O-methyl-
• 英文别名: 2,3,4-tri-O-methyl-meso-xylitol；2,3,4-tri-O-methyl-xylitol；2,3,4-tri-O-methylxylitol
• CAS: 14550-95-9；20227-09-2；20704-03-4；52525-61-8
• 化学式: C₈H₁₈O₅
• 分子量: 194.228
• InChiKey: UKEFEULBEWFWLP-JIGDXULJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.98
• 重原子数：
  13.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  L-Arabinitol, 2,3,4-tri-O-methyl- 在 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-methyl-xylitol
  参考文献：
  名称：

  Synthesis of l-arabinitol and xylitol monomers for the preparation of polyamides. Preparation of an l-arabinitol-based polyamide

  摘要：

  Dihydrochlorides of 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-methyl-L-arabinitol (and xylitol) and pentachlorophenyl esters of 2,3,4-tri-O-methyl-L-arabinaric (and xylaric) acids have been prepared as suitable bifunctional monomers for linear polycondensations. A new aregic AABB-type L-arabinitol-based polyamide is also described from the corresponding monomers. It was crystalline with T(m) 250 degrees C, optically active, and soluble in the usual organic solvents, including chloroform, and in water. Its M(w) obtained by GPC was 27,500 with a polydispersity of 1.4.

  DOI：

  10.1016/s0008-6215(01)00137-9
• 作为产物：
  描述：

  1,5-di-O-trityl-2,3,4-tri-O-methylxylitol 在 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 以92%的产率得到L-Arabinitol, 2,3,4-tri-O-methyl-
  参考文献：
  名称：

  通过结合双卟啉分子夹改进构型柔性二胺的立体化学分析。

  摘要：

  已通过NMR光谱结合构象去卷积分析了具有多个立体生成中心的无环二胺的相对立体化学。绑定到双卟啉分子夹子大大改善了立体化学分配。二胺是由廉价的糖醇合成的，其稳定的盐酸盐通过用离子交换树脂处理而定量地转化为游离碱。

  DOI：

  10.1002/chem.201300533

文献信息

• Helianthoside from <i>Heliaster</i> <i>helianthus</i>, an asterosaponin with a C3′-sulphated pyranose
  作者：M. Jesus Vazquez、Emilio Quinoa、Ricardo Riguera、Aurelio San Martin

  DOI：10.1139/v93-151

  日期：1993.8.1

  A new asterosaponin, named helianthoside (1), has been isolated from the butanolic extract of the starfish Heliaster helianthus and its structure established on the basis of extensive spectroscopic experiments and chemical correlations. Helianthoside is the first asterosaponin with a C3′-sulphated xylopyranose. The absolute stereochemistry at C24 was determined by the Trost–Mosher method.

  从海星Heliaster helianthus的丁醇提取物中分离出一种新的asterosaponin，命名为helianthoside（1），并通过广泛的光谱实验和化学相关性确定了其结构。Helianthoside是第一种带有C3'-硫酸化木糖苷的asterosaponin。通过Trost-Mosher方法确定了C24的绝对立体化学。
• Synthesis of Functionalized Phospholane Oxides and Phosphorinane Oxides from 1,4- and 1,5-Di-O-Mesyloxy Compounds
  作者：Tadashi Hanaya、Karsten Schürrle、Hiroshi Yamamoto

  DOI：10.3987/com-06-s(o)28

  日期：——

  Treatment of 1,4-di-0-mesyl-2,3-di-O-methyl-L-threitol (8b) with phenylphosphine in the presence of sodium hydride in DMSO, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane 1-oxide (7), while the same treatment of 1,5-di-O-mesyl-2,3,4-tri-O-methyl-mesoxylitol (11b) provided 2,3,4-trimethoxy-1-phenylphosphorinane 1-oxide (14).
• Aspinall, Gerald Oliver; Fanous, Hany Kamal; Kumar, Nimal Savitri, Canadian Journal of Chemistry, 1983, vol. 61, p. 1858 - 1863
  作者：Aspinall, Gerald Oliver、Fanous, Hany Kamal、Kumar, Nimal Savitri、Puvanesarajah, Velupillai

  DOI：——

  日期：——
• Synthesis of l-arabinitol and xylitol monomers for the preparation of polyamides. Preparation of an l-arabinitol-based polyamide
  作者：Marı́a de Gracia Garcı́a-Martı́n、Rocı́o Ruiz Pérez、Elena Benito Hernández、Juan A Galbis

  DOI：10.1016/s0008-6215(01)00137-9

  日期：2001.7

  Dihydrochlorides of 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-methyl-L-arabinitol (and xylitol) and pentachlorophenyl esters of 2,3,4-tri-O-methyl-L-arabinaric (and xylaric) acids have been prepared as suitable bifunctional monomers for linear polycondensations. A new aregic AABB-type L-arabinitol-based polyamide is also described from the corresponding monomers. It was crystalline with T(m) 250 degrees C, optically active, and soluble in the usual organic solvents, including chloroform, and in water. Its M(w) obtained by GPC was 27,500 with a polydispersity of 1.4.
• Improved Stereochemical Analysis of Conformationally Flexible Diamines by Binding to a Bisporphyrin Molecular Clip
  作者：Sara Norrehed、Henrik Johansson、Helena Grennberg、Adolf Gogoll

  DOI：10.1002/chem.201300533

  日期：2013.10.18

  The relative stereochemistry of acyclic diamines with several stereogenic centers has been analyzed by NMR spectroscopy in combination with conformational deconvolution. Binding to a bisporphyrin molecular clip improves the stereochemical assignment significantly. The diamines were synthesized from inexpensive sugar alcohols, and their stable hydrochlorides were quantitatively converted into free bases

  已通过NMR光谱结合构象去卷积分析了具有多个立体生成中心的无环二胺的相对立体化学。绑定到双卟啉分子夹子大大改善了立体化学分配。二胺是由廉价的糖醇合成的，其稳定的盐酸盐通过用离子交换树脂处理而定量地转化为游离碱。