3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-talooctitol | 219826-07-0

• 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: 3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-talooctitol
• 英文别名: [(2R,3R,4R,5R,6R)-3,4,5-triacetoxy-6-ethynyl-tetrahydropyran-2-yl]methyl acetate；[(2R,3R,4R,5R,6R)-3,4,5-triacetyloxy-6-ethynyloxan-2-yl]methyl acetate
• CAS: 219826-07-0
• 化学式: C₁₆H₂₀O₉
• 分子量: 356.329
• InChiKey: HAVBGJDVNNVPRE-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-talooctitol 在 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 水 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]ethynyl]-1H-indazole-5-carboxylic acid
  参考文献：
  名称：

  [EN] MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  [FR] DÉRIVÉS DE MANNOSE POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES

  摘要：

  由公式(I)表示的化合物或其药学上可接受的盐：其中U、W、X、Y、Z、p和环A如权利要求1所定义。这些化合物对于治疗或预防细菌感染是有用的。公式(I)的变量如本文所述。药学上可接受的组合物包括公式(I)的化合物或其药学上可接受的盐以及药学上可接受的载体、辅料或载体。治疗细菌感染的方法使用这些化合物或其药学上可接受的盐。

  公开号：

  WO2016199105A1
• 作为产物：
  描述：

  乙酸酐 、 (2R,3S,4R,5S,6R)-2-ethynyl-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以73%的产率得到3,7-anhydro-4,5,6,8-tetra-O-acetyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-talooctitol
  参考文献：
  名称：

  [EN] MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  [FR] DÉRIVÉS DE MANNOSE POUR LE TRAITEMENT D'INFECTIONS BACTÉRIENNES

  摘要：

  由公式(I)表示的化合物或其药学上可接受的盐：其中U、W、X、Y、Z、p和环A如权利要求1所定义。这些化合物对于治疗或预防细菌感染是有用的。公式(I)的变量如本文所述。药学上可接受的组合物包括公式(I)的化合物或其药学上可接受的盐以及药学上可接受的载体、辅料或载体。治疗细菌感染的方法使用这些化合物或其药学上可接受的盐。

  公开号：

  WO2016199105A1

文献信息

• Mannose derivatives for treating bacterial infections
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US10407414B2

  公开（公告）日：2019-09-10

  The compounds represented by Formula (I) or pharmaceutically acceptable salts thereof: with U, W, X, Y, Z, p and ring A as defined in claim 1. Those compounds are useful for the treatment or prevention of bacteria infections. The variables of Formula (I) are as described herein. Pharmaceutically acceptable compositions comprise the compounds of Formula (I) or pharmaceutically acceptable salts thereof and pharmaceutically acceptable carriers, adjuvants, or vehicles. Methods of treating bacteria infections employ such compounds or pharmaceutically acceptable salts thereof.

  由式（I）代表的化合物或其药学上可接受的盐：U、W、X、Y、Z、p 和环 A 如权利要求 1 所定义。 这些化合物可用于治疗或预防细菌感染。 式（I）的变量如本文所述。 药学上可接受的组合物包括式（I）化合物或其药学上可接受的盐以及药学上可接受的载体、佐剂或载体。 治疗细菌感染的方法采用此类化合物或其药学上可接受的盐。
• Novel Type of Rigid C-Linked Glycosylacetylene−Phenylalanine Building Blocks for Combinatorial Synthesis of C-linked Glycopeptides
  作者：Todd Lowary、Morten Meldal、Arnim Helmboldt、Andrea Vasella、Klaus Bock

  DOI：10.1021/jo980517h

  日期：1998.12.1

  C-linked 3- and 4-(glycosylacetylene)-Fmoc-phenylalanines were synthesized as rigid building blocks for synthesis of libraries of neoglycopeptide templates. Perbenzylated 1,5-galactonolactone, 1,5-gluconolactone, and 1,5-mannonolactone were reacted with cerium TMS-acetylide and the products reduced to the C-glycosylacetylene-TMS derivatives. The gluco and galacto configurations yielded exclusively the beta-C-glycoside, whereas the mannonolactone gave a mixture of alpha-C- and beta-C-anomer. The products were subjected to acetolysis and TMS cleavage. The resulting peracetylated glycosylacetylenes were cross-coupled with the (R,S)-N-alpha-acetyl-3- and 4-iodophenylalanine O-methyl esters by Pd(0) catalysis in piperidine to give the eight possible C-linked glycosyl amino acid building blocks 33-40 as diastereomeric pairs. These were O-deacetylated. As an example of further conversion into neoglycopeptide templates the N-acetyl group of the 4-linked galacto-diastereomeric pair 43 was hydrolyzed selectively by acylase 1 and separated from the (R)stereoisomer. The product was converted to 4-(beta-C-galactosylacetylene)(N-alpha-Fmoc-)-L-phenylalanine (52) by reaction with Fmoc-OSu. Acid hydrolysis of galactosyl acetylene phenyl alanine 43 at elevated temperature afforded the conversion of the acetylene to the 1'-oxo derivative which was also N-alpha-Fmoc protected. The building blocks were used in the glycopeptide synthesis of three neoglycopeptide templates 54, 55, and 56 known to bind to murine MHC class II E-k and to present the glycan for interaction with the T-cell receptor. This template has previously been employed to elicit a carbohydrate specific T-cell response.
• MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：EP3307733B1

  公开（公告）日：2021-10-20