1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-2-hydroxyethane | 35023-69-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-2-hydroxyethane
• 英文别名: (2-hydroxyethyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；2-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；1-(ethan-2'-ol)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；ethan-2'-ol 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-hydroxyethoxy)oxan-2-yl]methyl acetate
• CAS: 35023-69-9；55062-10-7；91364-05-5
• 化学式: C₁₆H₂₄O₁₁
• 分子量: 392.36
• InChiKey: FGWDENPSBRTVSA-LJIZCISZSA-N

物化性质

• 熔点：
  101-103 °C
• 沸点：
  475.5±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-2-hydroxyethane 反应 12.0h， 以66%的产率得到1,2-O-(2,3,4,6-tetra-O-acetyl-D-glucopyranosylidene)ethanediol
  参考文献：
  名称：

  新合成的螺旋原酸酯中的d-葡糖苷，光环化立体选择性d'羟烷基-d-葡糖苷

  摘要：

  摘要在氧化汞（II）和碘的存在下照射羟烷基葡糖苷可得到葡糖苷化的C-1-螺原酸酯。在起始糖苷具有CH2OH的情况下，环化通过α攻击具有区域和立体特异性。C-1-螺原酸酯可容易地以“一锅合成”的形式从葡糖基卤化物获得。

  DOI：

  10.1016/0008-6215(84)85081-8
• 作为产物：
  描述：

  乙二醇 生成 1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-2-hydroxyethane
  参考文献：
  名称：

  HEIKER, F. -R.;STOLTEFUSS, J.;FRANCKOWIAK, G.;SCHRAMM, M.;THOMAS, G.;GROS+

  摘要：

  DOI：

文献信息

• [EN] SYNTHESIS AND USE OF GLYCOSIDE PRO-DRUG ANALOGS<br/>[FR] SYNTHÈSE ET UTILISATION D'ANALOGUES GLYCOSIDES DE PROMÉDICAMENT
  申请人：NUTEK PHARMA LTD

  公开号：WO2012142141A1

  公开（公告）日：2012-10-18

  The present invention relates to methods and compositions for the synthesis, production, and use of pro-drug analogs. This invention relates to a method for the production of a broad group of glycosylated drugs, including but not limited to propofol, acetaminophen, and camptothecin carbohydrate derivatives.

  本发明涉及用于合成、生产和使用前药类似物的方法和组合物。本发明涉及一种用于生产包括但不限于丙泊酚、对乙酰氨基酚和喜树碱糖衍生物在内的广泛群体的糖基药物的方法。
• Synthesis And Use Of Glycoside Derivatives of Propofol
  申请人：Shull Brian

  公开号：US20120264702A1

  公开（公告）日：2012-10-18

  The present invention relates to methods and compositions for the synthesis, production, and use of pro-drug propofol analogs. This invention relates to a method for the production of a broad group of glycosylated propofol carbohydrate derivatives.

  本发明涉及一种用于合成、生产和使用前药丙泊酚类似物的方法和组合物。该发明涉及一种用于生产广泛羟乙基化丙泊酚碳水化合物衍生物的方法。
• Spacer-modified oligosaccharides with basic anchoring groups are inhibitors for endo-glycanases: Porcine pancreatic alpha-amylase as model enzyme
  作者：Jochen Lehmann、Markus Schmidt-Schuchardt

  DOI：10.1016/0008-6215(95)00089-c

  日期：1995.10

  By coupling methyl 2,3,6-tri-O-acetyl-4-O-(5-azido-6-p-tolysulfonyloxyhexyl)-alpha-D-glucopyranoside with 2-benzoylthioethyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside, a spacer-modified disaccharide derivative, methyl 4-O-(5-azido-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, was obtained and then enzymatically glucosylated to yield the spacer-modified tri- and tetra-saccharide methyl 4-O-(5-azido-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-azido-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, respectively, the extended spacer spanning the length of two (1 --> 4)-linked pyranosyl units. The corresponding amines methyl 4-O-(5-amino-9-alpha-D-glucopyranosyloxy-7-thianonyl)-alpha-D-glucopyranoside, methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside and methyl 4-O-(5-amino-9-alpha-maltotriosyloxy-7-thianonyl)-alpha-D-glucopyranoside, obtained by catalytic reduction, carry the basic functionality in a spacer position to allow ionic interaction with a catalytically active acidic group in porcine pancreatic alpha-amylase (PPA). Optimal inhibition of enzymic activity is by methyl 4-O-(5-amino-9-alpha-maltosyloxy-7-thianonyl)-alpha-D-glucopyranoside where three of the five subsites are occupied by glucosyl units and the spacer spanning the remaining subsites positions the amino group near the catalytic site.
• Synthesis and NMR characterization of hydroxyurea and mesylglycol glycoconjugates as drug candidates for targeted cancer chemotherapy
  作者：Bernd L. Sorg、William E. Hull、Hans-Christian Kliem、Walter Mier、Manfred Wiessler

  DOI：10.1016/j.carres.2004.11.024

  日期：2005.2

  Tumor targeting of glycoconjugated antineoplastic agents is a strategy currently under investigation for cancer chemotherapy. We have synthesized the glucosides and galactosides of the clinically established drug hydroxyurea and of mesylglycol, the reactive moiety of the anticancer drug busulfan. Glycosides of hydroxyurea were obtained by carbamoylation of hydroxylamine glycosides. The glycosides of mesylglycol were synthesized by mesylation of protected glycol glycosides. All compounds were characterized by detailed H-1 and C-13 NMR analysis. (C) 2004 Published by Elsevier Ltd.
• A Sugar Decorated Macromolecular Bottle Brush by Carbohydrate-Initiated Cationic Ring-Opening Polymerization
  作者：Christine Weber、Justyna A. Czaplewska、Anja Baumgaertel、Esra Altuntas、Michael Gottschaldt、Richard Hoogenboom、Ulrich S. Schubert

  DOI：10.1021/ma202401x

  日期：2012.1.10

  The capability of a range of protected glucose- (Glc), galactose- (Gal), and fructose- (Fm) based tosylates and triflates to initiate the living cationic ring-opening polymerization of 2-ethy1-2-oxazoline (EtOx) was investigated by detailed kinetic studies utilizing H-1 and F-19 NMR spectroscopy and SEC as well as MALDI and ESI TOF mass spectrometry. The Glc and Gal tosylates and a sterically hindered Fm triflate revealed slow and incomplete initiation, whereas the Glc and Gal triflates resulted in living polymerizations. Well-defined Glc as well as Gal alpha-end-functionalized PEtOx was obtained after deprotection. Functionalization of the living oxazolinium chain ends with methacrylate anions resulted in a macromonomer that was applied for RAFT polymerization. Deprotection resulted in a comb polymer that is selectively functionalized with Glc at the ends of all side chains (DPbackbone = 13, DPside (chains) = 10, PDI = 1.11).