2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside | 143571-58-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-ol
• CAS: 143571-58-8
• 化学式: C₃₂H₄₂O₆Si
• 分子量: 550.767
• InChiKey: VASCAWKIRODIIE-UNKWROQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 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-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2R,3S,5S,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-one
  参考文献：
  名称：

  Synthesis and Selectin‐Blocking Activity of a Novel Analog of Sulfatide: 3‐C‐Carboxymethylgalactosyl Lipid

  摘要：

  The 3-C-carboxymethylgalactose derivative carrying the 2-(tetradecyl)hexadecyl residue, which was designed as a novel analog of sulfatide, was synthesized. A key intermediate, 3-C-carboxymethylgalactose, was prepared from the suitably protected galactose by Swern oxidation and Wittig-Horner carboxymethylenation, followed by stereoselective reduction of the double bond. The compound obtained showed much more potent activity as a selectin blocker than the 3-O-sulfogalactose derivative with 2-(tetradecyl)hexadecyl residue.

  DOI：

  10.1081/car-120026455
• 作为产物：
  描述：

  2-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 四丁基溴化铵 、 sodium hydride 、 二正丁基氧化锡 、 palladium dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 2-(trimethylsilyl)ethyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  球四糖四糖和末端三糖和二糖片段的合成。

  摘要：

  球四糖[β-D-GalNAc-（1-> 3）-alpha-D-Gal-（1-> 4）-beta-D-Gal-的2-（三甲基甲硅烷基）乙基（TMSEt）β-糖苷（1-> 4）-D-Glc]和末端三糖，以及末端二糖的甲基α-糖苷1，是由三氟甲磺酸银促进适当保护的半乳糖苷，galabioside和globotrioside的β-糖基化合成的醇与3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃半乳糖苷氯，然后除去保护基。用三氟乙酸-二氯甲烷除去三糖四糖苷和末端三糖的异头TMSEt基团，得到相应的半缩醛糖8和3。末端三糖的TMSEt糖苷通过1-乙酸盐转化，

  DOI：

  10.1016/0008-6215(94)90010-8

文献信息

• Synthetic Studies on Sialoglycoconjugates 90: Total Synthesis of Sulfated Glucuronyl Paraglobosides
  作者：Yukihiro Isogai、Tomoko Kawase、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1080/07328309608005705

  日期：1996.11

  stereocontrolled glycosidation, methyl (4-O-acetyl-2-O-benzoyl-3-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate)uronate (8) was prepared from methyl [2-(trimethylsilyl)ethyl β-D-glucopyranosid]uronate (3) via selective 4-O-acetylation, 2-O-benzoylation, 3-O-levulinoylation, removal of the 2-(trimethylsilyl)ethyl group and imidate formation. The glycosylation of 8 with 2-(trimethylsilyl)ethyl 2,4,6-tri-O-

  已经合成了3- O-磺基葡萄糖醛酸酰基副球糖苷衍生物（五糖）。设计用于在最后一步有效，立体控制苷化的简便的硫酸化重要的中间体，甲基（4- ø -乙酰基-2- ø -苯甲酰基-3- ö -levulinoyl-α-d吡喃葡糖基三氯乙酰亚胺酯）糖醛酸（8）为由[2-（三甲基甲硅烷基）乙基β-D-吡喃葡萄糖苷]尿酸酯（3）经选择性的4- O-乙酰化，2- O-苯甲酰化，3- O-乙酰丙酰化，去除2-（三甲基甲硅烷基）乙基制备和亚氨酸盐的形成。8的糖基化用三甲基甲硅烷基三氟甲磺酸酯与2-（三甲基甲硅烷基）乙基2,4,6-三-O-苄基-β-D-吡喃半乳糖苷（9）得到2-（三甲基甲硅烷基）乙基O-（甲基4 - O-乙酰基-2- O -苯甲酰基-3- O-乙酰丙酰基-β-D-吡喃葡萄糖基尿酸酯）-（1→3）-2,4,6-三-O-苄基-β-D-吡喃半乳糖苷（10），通过除去苄基，苯甲酰化，去除2-（三甲基
• Catalytic conversions of diazosugars
  作者：Hilbert M. Branderhorst、Johan Kemmink、Rob M.J. Liskamp、Roland J. Pieters

  DOI：10.1016/s0040-4039(02)02407-3

  日期：2002.12

  Catalytic diazo decomposition chemistry was explored with novel diazoacetate functionalized carbohydrates. In both glucose and galactose derivatives, aromatic cycloadditions with the benzyl protecting groups proved to be most favorable reactions. Replacing the benzyl groups by methoxy groups in the glucose system led to formation of 'carbene dimers'. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of a Potent Antagonist of E-Selectin
  作者：Stephen Hanessian、Vincent Mascitti、Olivier Rogel

  DOI：10.1021/jo0110956

  日期：2002.5.1

  A synthesis of an antagonist of E-selectin previously reported by a group at Novartis Pharma in Basel is described. An important feature involves the formation of an ether linkage based on a Rh-II-catalyzed reaction. Stereocontrolled glycosylations rely on the anomeric activation of 2-pyridylthio carbonate as leaving group for the attachment of beta-D-galactopyranosyl and alpha-L-fucopyranosyl units on a common 1,5-anhydro D-glucitol scaffold.
• Misra, Anup Kumar; Mukherjee, Indrani; Mukhopadhyay, Balaram, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 1, p. 90 - 92
  作者：Misra, Anup Kumar、Mukherjee, Indrani、Mukhopadhyay, Balaram、Roy, Nirmolendu

  DOI：——

  日期：——
• Stereocontrolled synthesis of sialyl Lewis X ceramide consisting of a pentasaccharide recognized by the selectin family
  作者：Akira Hasegawa、Takashi Ando、Akihiko Kameyama、Makoto Kiso

  DOI：10.1016/s0008-6215(00)90524-x

  日期：1992.6