2,3,4,6-tetra-O-benzyl-1-C-methyl-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-1-C-methyl-D-glucopyranoside
• 英文别名: 3,4,5,7-Tetra-O-benzyl-1-deoxy-D-gluco-2-heptulopyranose；3,4,5,7-Tetra-O-benzyl-1-deoxy-D-gluco-heptulopyranose；(3R,4S,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• 化学式: C₃₅H₃₈O₆
• 分子量: 554.683
• InChiKey: SYOICKCXPGKAOU-BMURFIBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-C-methyl-D-glucopyranoside 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-methane β anomer
  参考文献：
  名称：

  基于构象限制策略的有效合成β-C-糖苷的方法：路易斯酸以完全的立体选择性促进硅烷还原异头位置。

  摘要：

  [反应：参见正文]当底物在（4）C（1）中构象受限时，通过Et（3）SiH / TMSOTf还原具有异头碳取代基的糖基内酯完全立体选择性生成相应的β-C-糖苷。 ）-椅子形式由3,4-O-环双缩酮或4,6-O-亚苄基保护基组成。因此，在构象限制策略的基础上实现了β-C-糖苷的有效构建。

  DOI：

  10.1021/ol048525+
• 作为产物：
  描述：

  2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 在 lithium aluminium tetrahydride 、 二甲基二环氧乙烷 作用下， 生成 2,3,4,6-tetra-O-benzyl-1-C-methyl-D-glucopyranoside
  参考文献：
  名称：

  Studies on the synthesis of C-Glycoside sulfones as potential glycosyl transferase inhibitors

  摘要：

  beta-C-Glycoside sulfoxides and sulfones were prepared by radical addition of thiol acetic acid to exocyclic glycals followed by deacetylation, S-alkylation, and selective oxidation. These compounds are representative examples of a new class of molecules designed to be glycosyl transferase inhibitors. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01021-1

文献信息

• Reaction of pyranoid and furanoid aldonolactones with chloromethyltrimethylsilane-derived reagents
  作者：Brigitte I. Glänzer、René Csuk

  DOI：10.1016/0008-6215(91)80007-a

  日期：1991.11

  Abstract Reaction of pyranoid and furanoid aldonolactones with trimethylsilylmethyl-lithium provides a convenient route to carbon-chain-elongated methyl ketones. Reaction of the lactones with chloro(trimethylsilyl)methyl-lithium gives the corresponding chloromethylketones.

  摘要吡喃类和呋喃类醛内酯与三甲基甲硅烷基甲基锂的反应为碳链加长的甲基酮的合成提供了一条方便的途径。内酯与氯代（三甲基甲硅烷基）甲基-锂反应，得到相应的氯代甲基酮。
• Stereoselective Synthesis of C- and N-Ketosides by Lewis Acid-Catalyzed C- and N-Glycosidation of Alkynyl, Phenyl, and Methyl Ketoses
  作者：Ana M. Gómez、Clara Uriel、Slawomir Jarosz、Serafín Valverde、J. Cristóbal López

  DOI：10.1002/ejoc.200300465

  日期：2003.12

  C-Ketosides can be prepared conveniently, in a stereoselective manner, from alkynyl, phenyl and methyl glucopyranose hemiketals by reaction with carbon nucleophiles in the presence of Lewis acids. The reaction of the hemiketals with trimethylsilyl azide provides an efficient route to the corresponding N-ketopyranosides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  C-酮苷可以通过与碳亲核试剂在路易斯酸存在下反应，以立体选择性方式方便地从炔基、苯基和甲基吡喃葡萄糖半缩酮制备。半缩酮与三甲基甲硅烷基叠氮化物的反应提供了获得相应 N-吡喃酮苷的有效途径。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Method of nucleating a polyolefin composition with acetal-based compounds
  申请人：Xie Chunping

  公开号：US20050239926A1

  公开（公告）日：2005-10-27

  An acetal-based composition useful as a nucleating, gelling, thickening or clarifying agent is disclosed. The composition may be synthesized or provided in many different forms, including multicarbon diacetals formed from carbohydrates. Once synthesized, the compound may be employed as an additive in a plastic composition, such as (for example) a polypropylene copolymer. Co-additives may also be employed. Several aryl structures may reside upon the hydrocarbon chain backbone. One structure of such an acetal-based composition which happens to have two aryl-containing groups is shown: wherein: n is 0, 1 or 2; Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl-containing groups; and R is selected from the group consisting of: alkenyls, alkyls, alkoxy, hydroxyl alkyls, and alkyl-halides.

  本发明揭示了一种基于缩醛的组合物，可用作成核、凝胶、增稠或澄清剂。该组合物可以合成或以许多不同的形式提供，包括由碳水化合物形成的多碳二缩醛。一旦合成，该化合物可以作为添加剂用于塑料组合物中，例如聚丙烯共聚物。也可以使用共添加剂。几种芳基结构可以存在于烃链骨架上。其中一种具有两个含芳基的基团的缩醛基组合物的结构如下所示：其中：n为0、1或2；Ar1和Ar2独立选择自取代或未取代的含芳基团；R选择自烯丙基、烷基、烷氧基、羟基烷基和烷基卤代物的群。
• Synthesis of C-disaccharides through dimerization of exo-glycals
  作者：Luigi Lay、Francesco Nicotra、Luigi Panza、Giovanni Russo、Enrico Caneva

  DOI：10.1021/jo00030a047

  日期：1992.2
• Stereoselective C-Allylation of 1-C-Alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoses with Allyltrimethylsilane
  作者：Takashi Yamanoi、Yoshiki Oda

  DOI：10.3987/com-01-9415

  日期：——

  The reaction of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyanoses with allyltrimethylsilane in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate gave the corresponding C-allylated C-alkyl glucopyranosides in good yields. This C-allylation proceeded with high alpha-stereoselectivity.