2,3,4,6-Tetra-O-benzyl-D-mannitol | 190952-23-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3,4,6-Tetra-O-benzyl-D-mannitol
• 英文别名: (2R,3R,4R,5R)-2,3,4,6-tetrakis(phenylmethoxy)hexane-1,5-diol
• CAS: 190952-23-9
• 化学式: C₃₄H₃₈O₆
• 分子量: 542.672
• InChiKey: MQOUZFJJURBWAX-YFRBGRBWSA-N

物化性质

• 沸点：
  695.8±55.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-Tetra-O-benzyl-D-mannitol 在 samarium diiodide 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  Diastereoselectivity of the cyclization of hexos-5-uloses by Sm2-mediated pinacol coupling

  摘要：

  2,3,4,6-Tetra-O-benzyl-hexos-5-uloses derived from D-glucose, D-mannose and D-galactose have been cyclized to cis-diols by a one pot Swern oxidation/SmI2-mediated pinacol coupling procedure. The effect of the substituent orientation on the diastereoselectivity of the coupling step is examined. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00161-0
• 作为产物：
  描述：

  甲基-D-丙噻 在 sodium tetrahydroborate 、 硫酸 、 sodium hydride 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.5h， 生成 2,3,4,6-Tetra-O-benzyl-D-mannitol
  参考文献：
  名称：

  GABA A受体离子通道的新型抑制剂-脱乙酰-扇贝苷的全合成

  摘要：

  通过将衍生自甲基α-d-甘露吡喃糖苷的二糖样片段与羟基庚基水杨酸片段偶联，完成了包含β-d-甘露吡喃糖苷单元的脱乙酰-伞花苷（1）的全合成。还已经评估了1的生物活性。

  DOI：

  10.1016/0040-4039(96)00316-4

文献信息

• Stereospecific cyclization to form C-furanosides
  作者：Bing-Hui Yang、Ji-Qing Jiang、Kan Ma、Hou-Ming Wu

  DOI：10.1016/0040-4039(95)00413-7

  日期：1995.4

  A cyclization of benzyl ethers with Sn2 active site at γ-position to form C-furanoside was studied.

  研究了在γ位具有S n 2活性位的苄基醚的环化反应，形成C-呋喃糖苷。
• Intramolecular Tishchenko Reactions of Protected Hexos-5-uloses: a Novel and Efficient Synthesis of l-Idose and l-Altrose
  作者：M. Adinolfi、G. Barone、F. De Lorenzo、A. Iadonisi

  DOI：10.1055/s-1999-3156

  日期：1999.3

  Protected t-butyl esters of aldonic acids with the rare L-ido and L-altro configuration can be effectively obtained by a diastereoselective Tishchenko reaction of hexos-5-uloses induced by t-BuOSmI2. These compounds can be easily converted into the corresponding protected lactones and free sugars.

  可以通过t-BuOSmI2诱导的六碳糖5-酮糖的立体选择性Tishchenko反应，有效地获得具有稀有L-ido和L-altro构象的戊酸的保护叔丁基酯。这些化合物可以容易地转化为相应的保护内酯和游离糖。
• Total synthesis of deacetyl-caloporoside, a novel inhibitor of the GABAA receptor ion channel
  作者：Kuniaki Tatsuta、Shohei Yasuda

  DOI：10.1016/0040-4039(96)00316-4

  日期：1996.4

  The total synthesis of deacetyl-caloporoside (1) which contains a β-d-mannopyranoside unit has been accomplished by coupling of the disaccharide-like segment derived from methyl α-d-mannopyranoside, with the hydroxyheptadecyl salicylic acid segment. The biological activity of 1 has also been evaluated.

  通过将衍生自甲基α-d-甘露吡喃糖苷的二糖样片段与羟基庚基水杨酸片段偶联，完成了包含β-d-甘露吡喃糖苷单元的脱乙酰-伞花苷（1）的全合成。还已经评估了1的生物活性。
• Synthesis of β-<i>CF</i>₂-<scp>d</scp>-Mannopyranosides and β-<i>CF</i>₂-<scp>d</scp>-Galactopyranosides by Reformatsky Addition onto 5-Ketohexoses
  作者：Eric Leclerc、Navnath Karche、Camille Pierry、Florent Poulain、Hassan Oulyadi、Xavier Pannecoucke、Jean-Charles Quirion

  DOI：10.1055/s-2006-958414

  日期：2007.1

  The first synthesis of β-CF 2 -d-manno- and β-CF 2 -d-galactopyranosylesters 1a and 1b is reported. It involves an oxidation-Reformatsky addition sequence on carbohydrate-derived diols and a dehydroxylation of the resulting cyclized compounds. The expected β-CF 2 -d-glycoside and an undesired β-CF 2 -l-glycoside are obtained from this sequence. An application of this methodology to the synthesis of some fluorinated pseudo-glycopeptides, potential selectin inhibitors, is also described.

  报告了第一个β-CF2-d-甘露糖和β-CF2-d-半乳糖苷的合成1a和1b。它涉及碳水化合物衍生的二醇的氧化-雷马茨基加成序列和所得环化化合物的脱羟基化。预期的β-CF2-d-糖苷和不需要的β-CF2-l-糖苷从该序列中获得。还描述了将这种方法应用于一些氟化假糖肽（潜在的选素抑制剂）的合成。
• Stereocontrolled Formation of Protected Aminodeoxyalditols from Simple Carbohydrate Precursors by Debenzylating Cycloetherification
  作者：Zhijie Fang、Yuhua Jiang、Qiangang Zheng、Hailang Jia、Jie Cheng、Baohui Zheng

  DOI：10.1055/s-0029-1217605

  日期：——

  A new and highly efficient methodology for the stereocontrolled synthesis of aminodeoxyalditols is described through a dimesylation/intramolecular SN2 nucleophilic substitution ring-forming reaction sequence from glucose, mannose, and galactose derivatives. The degree of difficulty and rate of the reaction of dimesylates in the cyclization process is evaluated and shows the trend: galactose > glucose > mannose derivatives, which has been identified from our experiments and classical theories.

  通过葡萄糖、甘露糖和半乳糖衍生物的二甲基化/分子内SN2亲核取代成环反应序列，描述了一种新的、高效的氨基脱氧醛醇立体控制合成方法。对环化过程中二甲基化合物的反应难度和速率进行了评估，结果表明：半乳糖>葡萄糖>甘露糖衍生物，这一结论已通过实验和经典理论得到证实。