甲基 6-O-[(叔丁基)二苯基硅烷基]-ALPHA-D-吡喃葡萄糖苷三乙酸酯 | 790685-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基 6-O-[(叔丁基)二苯基硅烷基]-ALPHA-D-吡喃葡萄糖苷三乙酸酯
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside
• 英文别名: methyl 2,3,4-tri-O-acetyl-6-O-TBDPS-α-D-glucopyranose；Methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldiphenylsilyl-A-D-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-methoxyoxan-3-yl] acetate
• CAS: 790685-09-5
• 化学式: C₂₉H₃₈O₉Si
• 分子量: 558.701
• InChiKey: YEJYGCSQLCXHSL-DFLSAPQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲基 6-O-[(叔丁基)二苯基硅烷基]-ALPHA-D-吡喃葡萄糖苷三乙酸酯 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  Directing/protecting groups mediate highly regioselective glycosylation of monoprotected acceptors

  摘要：

  A directing/protecting group designed for regioselective functionalization of partially-protected glucopyrannosides has been successfully used to prepare disaccharides in high yields. Most importantly, it has been demonstrated that highly regioselective and stereoselective glycosylation can be achieved when disarmed donors are employed. This study demonstrates the ability of directing/protecting group to induce regioselective glycosylation of carbohydrates and opens the field to the design of other DPGs for other monosaccharides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.026
• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol 、 乙酸酐 在 氨基磺酸 作用下， 反应 0.25h， 以92%的产率得到甲基 6-O-[(叔丁基)二苯基硅烷基]-ALPHA-D-吡喃葡萄糖苷三乙酸酯
  参考文献：
  名称：

  高效的 酰化 和硫酸化 碳水化合物 使用 氨基磺酸，温和，环保 催化剂 在有机之下 溶剂无条件

  摘要：

  快速高效 酰化 的 碳水化合物衍生物 在存在以下条件下，使用化学计量的酰化剂制备游离糖和游离糖 氨基磺酸，对环境无害 催化剂，在有机 溶剂-无条件的报道。选择性的酰化和硫酸化硫酸具有优异的收率碳水化合物衍生物 也已经通过使用 氨基磺酸 作为 催化剂。反应速度快，收率优异。

  DOI：

  10.1039/c1gc15122c

文献信息

• Efficient Acetylation of Carbohydrates Promoted by Imidazole
  作者：Pallavi Tiwari、Rishi Kumar、Prakas R. Maulik、Anup Kumar Misra

  DOI：10.1002/ejoc.200500555

  日期：2005.10

  An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  据报道，由咪唑促进的碳水化合物衍生物和未受保护的还原糖的有效过-O-乙酰化。该反应条件已成功用于乙酰化含有酸敏感官能团的碳水化合物衍生物。在大多数情况下，获得的产率非常好。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Application of Ball Milling Technology to Carbohydrate Reactions: I. Regioselective Primary Hydroxyl Protection of Hexosides and Nucleoside by Planetary Ball Milling‡
  作者：Premanand Ramrao Patil、K. P. Ravindranathan Kartha

  DOI：10.1080/07328300802218713

  日期：2008.7

  Dry ball milling of hexosides with trityl chloride in the presence of DABCO or Na2CO3 has been found to result in their complete conversion to the respective 6-O-trityl ethers. Further wet grinding of the reaction mixture with Ac2O in the presence of DMAP led to the respective fully protected hexosides in good to excellent yields after isolation. It has been found to be an effective one-pot two-step synthesis under solvent-free condition. The speed of homogenization has been shown to highly influence the rate and outcome of the reaction, and commercially available planetary ball mill has been proved to be very convenient for carrying out the reaction under standardized and reproducible conditions.
• Facile conversion of O-silyl protected sugars into their corresponding formates using POCl3·DMF complex
  作者：Marta M. Andrade、M. Teresa Barros

  DOI：10.1016/j.tet.2004.07.056

  日期：2004.10

  The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex (POCl3DMF)-D-. was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselective O-formylation with this formylating agent. This conversion was also studied with a monosaccharide analogue. (C) 2004 Elsevier Ltd. All rights reserved.
• Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions
  作者：Abhishek Santra、Goutam Guchhait、Anup Kumar Misra

  DOI：10.1039/c1gc15122c

  日期：——

  fast and efficient acylation of carbohydrate derivatives and free sugars using a stoichiometric quantity of acylating agents in the presence of sulfamic acid, an environmentally benign catalyst, under organic solvent-free conditions is reported. Excellent yields in the selective acylation and sulfation of carbohydrate derivatives have also been achieved using sulfamic acid as the catalyst. The reaction

  快速高效 酰化 的 碳水化合物衍生物 在存在以下条件下，使用化学计量的酰化剂制备游离糖和游离糖 氨基磺酸，对环境无害 催化剂，在有机 溶剂-无条件的报道。选择性的酰化和硫酸化硫酸具有优异的收率碳水化合物衍生物 也已经通过使用 氨基磺酸 作为 催化剂。反应速度快，收率优异。
• Directing/protecting groups mediate highly regioselective glycosylation of monoprotected acceptors
  作者：Janice Lawandi、Sylvain Rocheleau、Nicolas Moitessier

  DOI：10.1016/j.tet.2011.07.026

  日期：2011.10

  A directing/protecting group designed for regioselective functionalization of partially-protected glucopyrannosides has been successfully used to prepare disaccharides in high yields. Most importantly, it has been demonstrated that highly regioselective and stereoselective glycosylation can be achieved when disarmed donors are employed. This study demonstrates the ability of directing/protecting group to induce regioselective glycosylation of carbohydrates and opens the field to the design of other DPGs for other monosaccharides. (C) 2011 Elsevier Ltd. All rights reserved.