Bn(-2)[Bn(-3)][TBDMS(-4)]a-Glc1Me | 305815-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bn(-2)[Bn(-3)][TBDMS(-4)]a-Glc1Me
• 英文别名: [(2R,3R,4R,5R,6S)-3-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methanol
• CAS: 305815-34-3
• 化学式: C₂₇H₄₀O₆Si
• 分子量: 488.697
• InChiKey: LZVHKAVPHSFQJU-RTJMFUJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  Bn(-2)[Bn(-3)][TBDMS(-4)]a-Glc1Me 在 四丁基氟化铵 、 sodium hydride 作用下， 生成 (2S,3R,4S,5R,6R)-3,4-Bis-benzyloxy-5-hex-5-enyloxy-2-methoxy-6-vinyl-tetrahydro-pyran
  参考文献：
  名称：

  Cross-metathesis and ring-closing metathesis of olefinic monosaccharides

  摘要：

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01617-9
• 作为产物：
  描述：

  (2S,3R,4R,5R,6R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-tetrahydro-pyran 在 camphor-10-sulfonic acid 作用下， 以 甲醇 为溶剂， 以95%的产率得到Bn(-2)[Bn(-3)][TBDMS(-4)]a-Glc1Me
  参考文献：
  名称：

  Cross-metathesis and ring-closing metathesis of olefinic monosaccharides

  摘要：

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01617-9

文献信息

• Synthesis of<scp>l</scp>-Pyranosides from 5-Enopyranosides by Diastereoselective Hydroboration/Oxidation
  作者：Shiro Ikegami、Hideyo Takahashi、Namisa Miyama、Haruhiko Mitsuzuka

  DOI：10.1055/s-2004-834889

  日期：——

  Improved synthesis of L-pyranosides utilizing diastereoselective hydroboration/oxidation of 5-enopyranosides was investigated. A unique phenomenon in the diastereoselectivity of the hydroboration was incidentally found. The method was successfully applied to the synthesis of L-iduronic acid.

  研究了利用 5-enopyranosides 的非对映选择性硼氢化/氧化改进 L-pyranosides 的合成。偶然发现了硼氢化的非对映选择性的独特现象。该方法成功应用于L-艾杜糖醛酸的合成。
• Radical Decarboxylative Cyanomethylation of Aliphatic Carboxylic Acids and Uronic Acids via Vinyl Azide Cascade Fragmentation
  作者：Linhua Xu、Qishuai Li、Dongwei Li、Xin Zhou、Ni Song、Peng Wang、Ming Li

  DOI：10.1002/cjoc.202200732

  日期：——

  A direct oxidative radical decarboxylative cyanomethylation of carboxylic acids is described using 3-azido-2-methylbut-3-en-2-ol as the carbon-centered radical acceptor. The transformation is applicable to structurally diverse α-amino acids, α-oxy acids, α-keto acids, pentofuranuronic acids, and hexopyranuronic acids. The mechanistic investigations suggest that a radical process is involved in the

  使用 3-azido-2-methylbut-3-en-2-ol 作为以碳为中心的自由基受体，描述了羧酸的直接氧化自由基脱羧氰甲基化。该转化适用于结构多样的α-氨基酸、α-含氧酸、α-酮酸、戊呋喃糖醛酸和己吡喃糖醛酸。机械研究表明，转变涉及一个激进的过程。这项工作为构建具有生物学相关性的β-氨基酸、5-脱氧-己呋喃糖和 6-脱氧-庚糖提供了一种潜在的方法。
• 1-Fluoropyridinium triflates: versatile reagents for transformation of thioglycoside into O-glycoside, glycosyl azide and sulfoxide
  作者：Hirokazu Tsukamoto、Yoshinori Kondo

  DOI：10.1016/s0040-4039(03)01206-1

  日期：2003.7

  O-Fluoropyridinium triflates are versatile reagents to transform thioglycoside into O-glycoside, glycosyl azide and sulfoxide. The electronic nature of the substituents on the pyridine ring can control their ability to activate thioglycosides. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of a Trisaccharide Library by Using a Phenylsulfonate Traceless Linker on Synphase Crowns
  作者：Takashi Takahashi、Hitoshi Inoue、Yuichi Yamamura、Takayuki Doi

  DOI：10.1002/1521-3773(20010903)40:17<3230::aid-anie3230>3.0.co;2-z

  日期：2001.9.3

  44 members are in the trisaccharide library synthesized by the method described here. Six differently protected glucoside building blocks were sulfonylated with 1, coupled to the solid support 2 (a crown compound) by Pd0 -catalyzed carbonylative amidation, glycosylated twice, and cleaved from the sulfonate linker with four nucleophiles.
• Cross-metathesis and ring-closing metathesis of olefinic monosaccharides
  作者：Maarten H.D. Postema、Jared L. Piper

  DOI：10.1016/s0040-4039(02)01617-9

  日期：2002.9

  Cross-metathesis (CM) of a variety of carbohydrate-based C-6 and olefins with related C-1 and C-6 carbohydrate-based olefins proved to be unselective. CM was selective when all unhindered straight chain olefin was coupled with a carbohydrate-based C-6 olefin. When related short chain alkenols were tethered, via a Me2Si linker, to a Suitably protected carbohydrate-based C-6 olefin, good yields of ring-closed products were obtained with the second-generation Grubbs catalyst 3. A few examples where two carbohydrate-based olefinic alcohols were tethered via a Me2Si linker and subjected to ring-closing metathesis (RCM) have also been examined. (C) 2002 Elsevier Science Ltd. All rights reserved.