(3R,4R,5R)-3,4,6-tris(benzyloxy)hexane-1,5-diol | 911141-03-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4R,5R)-3,4,6-tris(benzyloxy)hexane-1,5-diol
• 英文别名: (3R,4R,5R)-3,4,6-tris(phenylmethoxy)hexane-1,5-diol
• CAS: 911141-03-2
• 化学式: C₂₇H₃₂O₅
• 分子量: 436.548
• InChiKey: RLTCJTPCCCUXJJ-ZONZVBGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3,4,6-tris(benzyloxy)hexane-1,5-diol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 (2S,3R,4R)-1-(2-(1H-imidazol-4-yl)ethyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)piperidine
  参考文献：
  名称：

  A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition

  摘要：

  A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselective reaction (de value > 98%). It is disclosed that bulky substituent at N atom of the piperidine decreases the inhibition activity except those substituents having the ability of salvation or forming disulfide bond with M444 at the active site of alpha-glycosidase, which enhance the interaction with enzyme. Compounds with S-configuration at C-3 show greater activity than those with R-configuration. The structure activity relationship study is also supported by molecular docking analysis. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.004
• 作为产物：
  描述：

  2-deoxy-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到(3R,4R,5R)-3,4,6-tris(benzyloxy)hexane-1,5-diol
  参考文献：
  名称：

  A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition

  摘要：

  A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselective reaction (de value > 98%). It is disclosed that bulky substituent at N atom of the piperidine decreases the inhibition activity except those substituents having the ability of salvation or forming disulfide bond with M444 at the active site of alpha-glycosidase, which enhance the interaction with enzyme. Compounds with S-configuration at C-3 show greater activity than those with R-configuration. The structure activity relationship study is also supported by molecular docking analysis. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.004

文献信息

• A Highly Efficient and Stereocontrolled Synthesis of 2-Deoxy-1,5-thioanhydro-L-hexitols fromD-Glycals in a Tandem Nucleophilic Displacement Reaction
  作者：Pietro Passacantilli、Clara Centore、Elena Ciliberti、Francesca Leonelli、Giovanni Piancatelli

  DOI：10.1002/ejoc.200600010

  日期：2006.7

  the corresponding 2-deoxy-1,5-thioanhydro-L-hexitols, while L-rhamnal gives 3,4-di-O-benzyl-2,6-dideoxy-1,5-thioanhydro-D-xylo-hexitol. This straightforward chemistry is shown to be useful for the synthesis of glycosyl derivatives of 2-deoxy-1,5-thioanhydro-L-hexitol, starting from glycosyl glycals such as D-lactal, D-cellobial, D-maltal, D-melibial and D-gentiobial, thus avoiding the usually lengthy

  2-Deoxy-1,5-thioanhydro-L-hexitols 以简明的顺序合成，包括：i) 用醋酸汞 (II)/硼氢化钠水溶液开环糖醛；ii) 多官能化开放中间体的游离羟基的甲磺酸化；iii) 用硫化钠处理S-杂环化。硫糖衍生物的产率为 60-80%。因此，D-glucal 和 D-galactal 可以转化为相应的 2-deoxy-1,5-thioanhydro-L-hexitols，而 L-rhamnal 产生 3,4-di-O-benzyl-2,6-dideoxy- 1,5-硫代脱水-D-木糖醇。这种直接的化学过程被证明可用于合成 2-脱氧-1,5-硫代脱水-L-己糖醇的糖基衍生物，从糖基糖基如 D-乳酸、D-纤维、D-麦芽糖、D-melibial 开始和 D-龙胆，从而避免了通常冗长的糖基化程序。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451
• Glycals in Organic Synthesis: A Systematic Strategy for the Preparation of Uncommon Piperidine 1,2-Dideoxy-L-azasugars and 2-Deoxy-1,5-anhydro-L-hexitols
  作者：Elena Ciliberti、Roberta Galvani、Francesca Gramazio、Samantha Haddas、Francesca Leonelli、Pietro Passacantilli、Giovanni Piancatelli

  DOI：10.1002/ejoc.200600959

  日期：2007.3

  A systematic synthetic strategy has been developed for producing uncommon piperidine 1,2-dideoxy-L-azasugars. This method involves the formation of open intermediates such as 2, 7, and 10 easily by ring-opening of D-glycals with aqueous mercury(II) acetate/sodium borohydride. A concise sequence of regioselective amination and cyclization reactions then allowed us to prepare the cyclic compounds 5a

  已经开发了一种用于生产罕见哌啶 1,2-双脱氧-L-氮杂糖的系统合成策略。该方法涉及通过 D-缩醛与乙酸汞 (II) 水溶液/硼氢化钠开环轻松形成开放中间体，例如 2、7 和 10。然后，区域选择性胺化和环化反应的简洁序列使我们能够制备环状化合物 5a 和 5b，天然存在的 fagomine 同系物的 L 对映异构体，如 3-epi-fagomine (II) 和 3,4-di-epi-fagomine (III) )，分别来自 D-glucal 和 D-galactal。非天然的 3,4-di-epi-6-deoxyfagomine 9 是通过相同的反应顺序从 L-鼠李醛中获得的。这种直接的化学反应已被证明可用于从糖基糖基（如 D-内酰胺、D-纤维糖醛）开始制备 1,2-二脱氧-L-氮杂糖的糖基衍生物。D-maltal 和 D-melibial，从而避免了通常冗长的糖基化程序。我们协议的
• [EN] SUGAR ALCOHOL DERIVATIVES, A PROCESS FOR PREPARING 3-DEOXY-2-OCTULOSONIC ACID AND 3-DEOXY-2-HEPTULOSONIC ACID COMPOUNDS AND DERIVATIVES
  申请人：RIJKSUNIVERSITEIT TE LEIDEN

  公开号：WO1991002741A1

  公开（公告）日：1991-03-07

  (EN) The invention provides a novel class of versatile intermediates, i.e. 1,4 cyclic sulfates of sugar alcohols having protected hydroxy groups, such as 1,4 cyclic sulfates of D-mannitol having protected 2-, 3-, 5- and 6-hydroxy groups and D-arabinitol having protected 2-, 3- and 5-hydroxy groups. The invention also provides methods for preparing 3-deoxy-2-octulosonic acid and 3-deoxy-2-heptulosonic acid compounds and derivatives, in which these novel 1,4 cyclic sulfates are used as intermediates.(FR) On décrit une nouvelle classe d'intermédiaires polyvalents, c'est-à-dire des suflates 1,4 cycliques d'alcools de sucre qui possèdent de groupes hydroxy protégés, tels que les sulfates 1,4 cycliques de mannitol possédant des groupes 2-, 3-, 5- et 6-hydroxy protégés et l'arabinitol possédant des groupes 2-, 3-, et 5-hydroxy portégés. On prévoit également des procédés de préparation de composés et de dérivés de l'acide 3-déoxy-2-octulosonique et de l'acide 3-déoxy-2-heptulosonique, ces nouveaux sulfates cycliques 1,4 étant utilisés comme intermédiaires.
• A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition
  作者：Fu-xiang Jiang、Qiao-zhen Liu、Dan Zhao、Cui-ting Luo、Cui-ping Guo、Wen-cai Ye、Cheng Luo、Heru Chen

  DOI：10.1016/j.ejmech.2014.03.004

  日期：2014.4

  A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselective reaction (de value > 98%). It is disclosed that bulky substituent at N atom of the piperidine decreases the inhibition activity except those substituents having the ability of salvation or forming disulfide bond with M444 at the active site of alpha-glycosidase, which enhance the interaction with enzyme. Compounds with S-configuration at C-3 show greater activity than those with R-configuration. The structure activity relationship study is also supported by molecular docking analysis. (C) 2014 Elsevier Masson SAS. All rights reserved.