ethyl 2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetate | 1251851-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetate
• CAS: 1251851-66-7
• 化学式: C₃₉H₄₂F₂O₈
• 分子量: 676.754
• InChiKey: SIJBKOUSZYASSN-YUIAHADPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  49.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 以78%的产率得到2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetic acid
  参考文献：
  名称：

  Assessing the ability of a short fluorinated antifreeze glycopeptide and a fluorinated carbohydrate derivative to inhibit ice recrystallization

  摘要：

  A short fluorinated antifreeze glycopeptide (2) was synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The activity of 2 was compared to native biological antifreeze AFGP 8 and a rationally designed C-linked AFGP analogue (OGG-Gal, 1). In addition, a simple fluorinated galactose derivative was prepared and its IRI activity was compared to non-fluorinated compounds. The results from this study suggest that the stereochemistry at the anomeric position in the carbohydrate plays a role in imparting ice recrystallization inhibition activity and that incorporation of hydrophobic groups such as fluorine atoms cause a decrease in IRI activity. These observations are consistent with the theory that fluorine atoms increase ordering of bulk water resulting in a decrease of IRI activity, supporting our previously proposed mechanism of ice recrystallization inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.148
• 作为产物：
  描述：

  Difluoro-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以81%的产率得到ethyl 2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetate
  参考文献：
  名称：

  Assessing the ability of a short fluorinated antifreeze glycopeptide and a fluorinated carbohydrate derivative to inhibit ice recrystallization

  摘要：

  A short fluorinated antifreeze glycopeptide (2) was synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The activity of 2 was compared to native biological antifreeze AFGP 8 and a rationally designed C-linked AFGP analogue (OGG-Gal, 1). In addition, a simple fluorinated galactose derivative was prepared and its IRI activity was compared to non-fluorinated compounds. The results from this study suggest that the stereochemistry at the anomeric position in the carbohydrate plays a role in imparting ice recrystallization inhibition activity and that incorporation of hydrophobic groups such as fluorine atoms cause a decrease in IRI activity. These observations are consistent with the theory that fluorine atoms increase ordering of bulk water resulting in a decrease of IRI activity, supporting our previously proposed mechanism of ice recrystallization inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.148

文献信息

• Glycopeptide derivatives for the preservation and protection of biological materials and microorganisms
  申请人：TFCHEM

  公开号：US10100088B2

  公开（公告）日：2018-10-16

  The present invention relates to a compound of the following formula (I): in which at least one and only one group chosen among R5, R6 and R7 is a group of the following formula: The present invention relates also to uses thereof for preservation and/or protection and/or regeneration of biological materials and or microorganisms and for cosmetic or dermatological applications such as anti-aging, skin protection and skin regeneration; to culture, storage and/or preservation media comprising such a compound; to cosmetic or dermatological compositions comprising such a compound; to processes for preparing such a compound; and to synthesis intermediates.

  本发明涉及以下式（I）的化合物： 其中R5、R6和R7中至少一个且仅有一个基团选择为以下式的基团： 本发明还涉及该化合物的用途，用于生物材料和/或微生物的保存和/或保护和/或再生以及用于化妆品或皮肤学应用，如抗衰老、皮肤保护和皮肤再生；包含这种化合物的培养、储存和/或保存培养基；包含这种化合物的化妆品或皮肤学组合物；制备这种化合物的方法；以及合成中间体。