(R)-1-((4S,4'S,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethanol | 3969-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((4S,4'S,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethanol
• 英文别名: 1,2:3,4-di-O-isopropylidene-L-rhamnitol；O³,O⁴;O⁵,O⁶-diisopropylidene-1-deoxy-L-mannitol；O³,O⁴;O⁵,O⁶-Diisopropyliden-1-desoxy-L-mannit；1,2,3,4-Di-O-isopropyliden-L-rhamnit；6-Deoxy-1,2:3,4-bis-O-(1-methylethylidene)-L-mannitol；(1S)-1-[(4S,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol
• CAS: 3969-60-6
• 化学式: C₁₂H₂₂O₅
• 分子量: 246.304
• InChiKey: GADAECXODUENSL-XKNYDFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((4S,4'S,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethanol 在 溶剂黄146 作用下， 生成 L-rhamnitol
  参考文献：
  名称：

  The Action of Acetobacter suboxydans upon ι-Desoxy Sugar Alcohols

  摘要：

  DOI：

  10.1021/ja01158a025
• 作为产物：
  描述：

  1-deoxy-D-gulitol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以6.05 g的产率得到(R)-1-((4S,4'S,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethanol
  参考文献：
  名称：

  Synthesis of novel l-rhamnose derived acyclic C-nucleosides with substituted 1,2,3-triazole core as potent sodium-glucose co-transporter (SGLT) inhibitors

  摘要：

  Sodium-glucose co-transporter (SGLT) inhibitors are a novel class of therapeutic agents for the treatment of type 2 diabetes by preventing renal glucose reabsorption. In our efforts to identify novel inhibitors of SGLT, we synthesized a series of L-rhamnose derived acyclic C-nucleosides with 1,2,3-triazole core. The key beta-ketoester building block 4 prepared from L-rhamnose in five steps, was reacted with various aryl azides to produce the respective 1,2,3-triazole derivatives in excellent yields. Deprotection of acetonide group gave the desired acyclic C-nucleosides 7a-o. All the new compounds were screened for their sodium-glucose co-transporters (SGLT1 and SGLT2) inhibition activity using recently developed cell-based nonradioactive fluorescence glucose uptake assay. Among them, 7m with IC50: 125.9 nM emerged as the most potent SGLT2 inhibitor. On the other hand compound 7d exhibited best selectivity for inhibition of SGLT2 (IC50: 149.1 nM) over SGLT1 (IC50: 693.2 nM). The results presented here demonstrated the utility of acyclic C-nucleosides as novel SGLT inhibitors for future investigations. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.077

文献信息

• Synthesis of <scp>l</scp>-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors
  作者：Siddamal Reddy Putapatri、Abhinav Kanwal、Balasubramanian Sridhar、Sanjay K. Banerjee、Srinivas Kantevari

  DOI：10.1039/c4ob01319k

  日期：——

  Herein we describe the synthesis of a series of novel fused bicyclic 1,2,3-triazoles from commercially available, natural deoxy sugar, L-rhamnose. The key reactions involved are (i) Zn(OTf)2 catalyzed enantioselective alkynylation of L-rhamnose derived azidoaldehyde and (ii) deprotection of the acid sensitive 1,2-isopropylidene group followed by in situ intramolecular click-cycloaddition of azidoalkynols

  本文中，我们描述了从市售的天然脱氧糖L-鼠李糖合成一系列新颖的稠合双环1,2,3-三唑。所涉及的主要反应是：（i）锌（OTF）2催化的对映选择性的炔基大号鼠李糖衍生的酸敏感性1,2-异亚丙基，随后的azidoaldehyde和（ii）脱保护原位azidoalkynols的分子内的点击环加成。一些化合物具有出色的钠葡萄糖转运蛋白（SGLT1和SGLT2）抑制活性。
• Synthesis of inhibitors of adenosine deaminase. A total synthesis of erythro-3-(adenin-9-yl)-2-nonanol and its isomers from chiral precursors
  作者：David C. Baker、L. D. Hawkins

  DOI：10.1021/jo00132a039

  日期：1982.5
• Aldol reactions on 1-deoxy-3,4:5,6-di-O-isopropylidene-l-fructose as a route to higher-carbon carbohydrates
  作者：Alan H. Haines、Andrew J. Lamb

  DOI：10.1016/s0008-6215(00)00014-8

  日期：2000.5

  With a view to preparing higher-carbon carbohydrates, crossed-aldol reactions of the methyl ketone 1-deoxy-3,4:5,6-di-O-isopropylidene-L-fructose with a representative series of aldehydes have been investigated, and the feasibility has been demonstrated of constructing a C-11 unit containing some of the key functionality found in the carbohydrate component of the herbicidins.