1,2,3,4-tetra-O-acetyl-7-bromo-6,7-dideoxy-α-D-manno-heptopyranoside | 540501-07-3

• 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-tetra-O-acetyl-7-bromo-6,7-dideoxy-α-D-manno-heptopyranoside
• 英文别名: 7-bromo-6,7-dideoxy-1,2,3,4-tri-O-acetyl-α-D-manno-heptopyranoside；[(2R,3R,4S,5S,6R)-4,5,6-triacetyloxy-2-(2-bromoethyl)oxan-3-yl] acetate
• CAS: 540501-07-3
• 化学式: C₁₅H₂₁BrO₉
• 分子量: 425.23
• InChiKey: HVXRBWJKLOIBGO-MRLBHPIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-acetyl-7-bromo-6,7-dideoxy-α-D-manno-heptopyranoside 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-(1,3-dithianyl)-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 硫酸 、 氢气 、 溶剂黄146 、 lithium bromide 作用下， 以 乙醇 、 水 、 乙腈 、 丁酮 为溶剂， 反应 47.33h， 生成 1,2,3,4-tetra-O-acetyl-7-bromo-6,7-dideoxy-α-D-manno-heptopyranoside
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297

文献信息

• A convenient synthetic route to mannose 6-phosphonate-cholesteryl conjugate
  作者：Sébastien Vidal、Alain Morère、Jean-Louis Montero

  DOI：10.1002/hc.10134

  日期：——

  is described involving (1) a one-carbon chain elongation at the 6-position of mannose, followed by (2) phosphonation, using tris(trimethylsilyl)phosphite. This method was shown to e efficient and provides a general route to various mannose 6-phosphonate-based compounds for the design of drug delivery systems. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:241–246, 2003; Published online in Wiley

  描述了基于甘露糖 6-膦酸酯的糖脂的多步合成，包括 (1) 在甘露糖的 6 位进行单碳链延长，然后 (2) 使用亚磷酸三(三甲基甲硅烷基)酯进行磷酸化。该方法被证明是有效的，并为设计药物递送系统的各种基于甘露糖 6-膦酸酯的化合物提供了通用途径。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:241–246, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10134
• [EN] MANNOSE 6-PHOSPHATE OR ASGPR RECEPTOR BINDING COMPOUNDS FOR THE DEGRADATION OF EXTRACELLULAR PROTEINS<br/>[FR] COMPOSÉS DE LIAISON AU RÉCEPTEUR MANNOSE-6-PHOSPHATE OU ASGPR POUR LA DÉGRADATION DE PROTÉINES EXTRACELLULAIRES
  申请人：[en]AVILAR THERAPEUTICS, INC.

  公开号：WO2023028338A2

  公开（公告）日：2023-03-02

  Compounds and compositions that have a mannose 6-phosphate receptor or ASGPR binding ligand bound to an extracellular protein binding ligand are provided for the selective degradation of a target extracellular protein in vivo to treat disorders mediated by the extracellular protein.