methyl 2,3-O-(diphenylmethylene)-α-L-rhamnopyranoside | 148777-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3-O-(diphenylmethylene)-α-L-rhamnopyranoside
• 英文别名: methyl 2,3-O-diphenylmethylene-α-L-rhamnopyranoside；(3aR,4R,6S,7S,7aR)-4-methoxy-6-methyl-2,2-diphenyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 148777-95-1
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: KLTFUKFWUUNJCD-RKWNZTQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-(diphenylmethylene)-α-L-rhamnopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 methyl 2-O-diphenylmethyl-4-O-methyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis and Hydrogenolysis of Dioxolane-Type Diphenyl-Methylene and Fluoren-9-Ylidene Carbohydrate Acetals Containing a Neighbouring Substituted Hydroxyl Function

  摘要：

  Series of dioxolane-type diphenylmethylene and fluoren-9-ylidene acetals of hexoses containing adjacent O-alkyl, deoxy or hydroxy functions were prepared and hydrogenolysed with the LiAlH4-AlCl3 reagent. The observed direction of ring-cleavage was discussed in terms of different influences, such as complex formation and orientation of the hydride reagent, the configurational arrangements of the free OH group to one of the oxygen atoms of the dioxolane ring, as well as the conformational relationship of the rings present in the 1,6-anhydro derivatives.

  DOI：

  10.1080/07328309708005742
• 作为产物：
  描述：

  苯甲酮二甲基缩酮 、 甲基-Alpha-D-吡喃鼠李糖苷 在 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 生成 methyl 2,3-O-(diphenylmethylene)-α-L-rhamnopyranoside
  参考文献：
  名称：

  A kinetic study on the reductive opening of the diphenylmethylene acetal in methyl 2,3-O-diphenylmethylene-α-l-rhamnopyranoside

  摘要：

  Reductive opening of the diphenylmethyl acetal in methyl 2,3-O-diphenylmethylene-alpha-L-rhamnopyranoside has been investigated by kinetic studies, and the results have been compared to those recently obtained by quantum chemical calculations. In contrast to the previous theoretical calculations which related only to the presumably rate limiting step of the reductive opening, the reaction system LiAlH4, AlCl3, and the title compound consists of at least four simultaneous reactions. Nevertheless, reasonable agreement can be found between the activation Gibbs free energy obtained from kinetic measurements and the theoretically calculated ones in spite of the experimental errors and the approximate nature of theoretical calculations. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.041

文献信息

• Block Synthesis of Tetra- and Hexasaccharides (β-<scp>d</scp>-Glycero-<scp>d</scp>-manno-Hep<i>p</i>-(1→4)-[α-<scp>l</scp>-Rha<i>p</i>-(1→3)-β-<scp>d</scp>-glycero-<scp>d</scp>-manno-Hep<i>p</i>-(1→4)]_<i>n</i>-α-<scp>l</scp>-Rha<i>p</i>-OMe (<i>n</i> = 1 and 2)) Corresponding to Multiple Repeat Units of the Glycan from the Surface-Layer Glycoprotein from Bacillus thermoaerophilus
  作者：David Crich、Ming Li

  DOI：10.1021/jo801414c

  日期：2008.9.19

  A fully stereocontrolled block synthesis of the title tetra- and hexasaccharides has been achieved taking advantage of the ability of the 4,6-O-benzylidene acetal to control the stereochemistry of the beta-D-glycero-D-mannoheptopyranoside unit and of a 2,3-O-diphenylmethylene acetal to install the alpha-L-rhamnopyranosidic linkages. Comparison of the spectral data for the hexasaccharide with that of the natural isolate confirms the structure of this very unusual and structurally challenging glycan.