1-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose | 213028-88-7

• 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: 1-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose
• 英文别名: 1-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose；1-O-acetyl-3,4,6-O-benzylglucopyranose；[(3R,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] acetate
• CAS: 213028-88-7
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: IENJTXRMTDRUSS-VIVFLBMVSA-N

物化性质

• 沸点：
  618.5±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.5h， 生成 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Study of Kaempferol Glycoside as an Insulin Mimic Reveals Glycon To Be the Key Active Structure

  摘要：

  Diabetes mellitus is increasing in prevalence with patient numbers rising throughout the world. Current treatments for-diabetes mellitus focus on control of blood glucose levels. Certain kinds of flavonoids or their glycosides stimulate cells to improve glucose uptake and lower blood glucose levels. We synthesized kaempferol 3-O-neohesperidoside (1) a naturally occurring substance present in Cyathea phalerata Mart., reported to mimic the action of insulin. Synthetic 1 promoted glucose uptake in the cultured cell line, L6. Further studies to determine the core structure responsible for this activity using synthetic compounds revealed neohesperidose to be the primary pharmacophore. These findings support the use of certain saccharides as a potential novel treatment for diabetes mellitus by replacing or supporting insulin.

  DOI：

  10.1021/ml100171x
• 作为产物：
  描述：

  1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose 在 盐酸 、 silica gel 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成 1-O-acetyl-3,4,6-tri-O-benzyl-α,β-D-glucopyranose
  参考文献：
  名称：

  Charette, Andre B.; Turcotte, Nathalie; Cote, Bernard, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 3, p. 421 - 432

  摘要：

  DOI：

文献信息

• A practical synthesis of β-d-mannopyranosides
  作者：Alois Fürstner、Ingo Konetzki

  DOI：10.1016/s0040-4039(98)01163-0

  日期：1998.8

  An indirect yet highly efficient protocol for the β-d-mannosylation of sterically hindered alcohols is reported. Trichloroacetimidate 5 is used a key building block which is converted into the desired mannosides 9 via triflates 8 by an ultrasound promoted β-d-gluco → β-d-manno inversion process.

  据报道，用于空间受阻醇的β- d-甘露糖基化的间接但高效的方案。三氯乙酰亚胺酯5被使用的密钥构建块被转换成期望的甘露糖苷9通过三氟甲磺酸酯8通过超声波促进β- d -葡糖→β- d -甘露反转处理。
• Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents
  作者：Gergely L. Tolnai、Ulf J. Nilsson、Berit Olofsson

  DOI：10.1002/anie.201605999

  日期：2016.9.5

  iodonium(III) reagents. Both electron‐withdrawing and electron‐donating aryl groups were introduced under ambient conditions and without precautions to exclude air or moisture. Furthermore, the approach was extended both to full arylation of cyclodextrin, and to trifluoroethylation of carbohydrate derivatives. This is the first general approach to introduce traditionally non‐electrophilic groups into

  使用稳定且易于制备的碘(III)试剂建立了碳水化合物衍生物O-功能化的新方法。吸电子芳基和供电子芳基都是在环境条件下引入的，并且没有采取措施排除空气或湿气。此外，该方法还扩展到环糊精的完全芳基化和碳水化合物衍生物的三氟乙基化。这是将传统非亲电基团引入糖主链周围的任何 OH 基团的第一个通用方法。该方法将适用于合成有机化学和生物化学，因为重要的官能团可以在简单而稳健的反应条件下以快速有效的方式掺入。
• Stereospecific Synthesis of α- and β-C-Glycosides from Glycosyl Sulfoxides:  Scope and Limitations
  作者：Mercedes Carpintero、Inés Nieto、Alfonso Fernández-Mayoralas

  DOI：10.1021/jo0014515

  日期：2001.3.1

  alpha-L-fuco-, alpha-D-gluco-, beta-D-gluco-, and alpha-D-mannopyranose have been synthesized from the corresponding glycosyl phenyl sulfoxide through phenylsulfinyl-lithium exchange, to generate an anomeric carbanion, and subsequent reaction with a carbon electrophile. The reactions were stereospecific and proceeded with retention of the configuration at the anomeric center. Improved yields of C-glycosides

  衍生自α-L-岩藻糖，α-D-葡萄糖-，β-D-葡萄糖-和α-D-甘露聚糖的C-糖苷是通过相应的糖基苯基亚砜通过苯亚磺酰基-锂交换合成的，以生成异头碳负离子，随后与碳亲电试剂反应。该反应是立体特异性的，并且在构型保持在异头中心处进行。通过逆添加方案获得提高的C-糖苷产率。用醛截留异头碳负离子的效果最佳。还研究了与酮，氯甲酸酯，腈和卤代烷的反应。讨论了反应的机理。
• Synthesis of a staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety
  作者：Samir Messaoudi、Fabrice Anizon、Bruno Pfeiffer、Roy Golsteyn、Michelle Prudhomme

  DOI：10.1016/j.tetlet.2004.04.102

  日期：2004.6

  The synthesis of a new staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety is described. This synthesis could be achieved by coupling a sugar moiety previously tosylated in 2′ position to the azaindolocarbazole aglycone. Nucleophilic substitution on the carbon bearing the tosyl group yielded to the key cyclization leading to a compound in which the carbohydrate part is

  描述了具有7-氮杂吲哚单元而不是吲哚部分的新星形孢菌素类似物的合成。该合成可以通过将先前在2'位置甲苯磺酸化的糖部分偶联至氮杂吲哚并咔唑糖苷配基来实现。带有甲苯磺酰基的碳上的亲核取代产生关键的环化作用，从而形成一种化合物，其中的碳水化合物部分同时与吲哚和氮杂吲哚氮原子相连。
• Synthesis of bridged aza-rebeccamycin analogues
  作者：Samir Messaoudi、Fabrice Anizon、Bruno Pfeiffer、Michelle Prudhomme

  DOI：10.1016/j.tet.2005.04.043

  日期：2005.7

  The syntheses of rebeccamycin analogues possessing a 7-azaindole moiety instead of an indole unit, and with both indole and azaindole moieties linked to the carbohydrate are described. In these bridged aza compounds, the oxygen of the pyranose heterocycle is oriented towards either the indole, or the azaindole unit. In these series, compounds bearing a free imide nitrogen were synthesized by coupling the corresponding aglycones with a sugar pre-tosylated in 2-position via a Mitsunobu reaction. To obtain a precursor for bridged aza-rebeccamycin analogues substituted in 6-position on the sugar moiety, a 2,6-ditosylated sugar was used. (c) 2005 Elsevier Ltd. All rights reserved.