4-methoxyphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: N-((2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-((4-methoxyphenyl)thio)tetrahydro-2H-pyran-3-yl)acetamide；N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-methoxyphenyl)sulfanyloxan-3-yl]acetamide
• 化学式: C₁₅H₂₁NO₆S
• 分子量: 343.401
• InChiKey: WPLNUWADHFKFQP-RYPNDVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,4'-二甲氧基二苯二硫 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 三苯基膦 、 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 1,4-二氧六环 、 水 、 二氯甲烷 为溶剂， 反应 18.0h， 以53%的产率得到4-methoxyphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-d-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride and aryl thiols or disulfides

  摘要：

  An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranosides has been devised from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride and arylthiols or aryl disulfides using phase transfer catalysis conditions. This simple procedure compresses up to three synthetic steps into a one-pot reaction, obviating the need for tedious workups and chromatography and directly furnishes crystalline materials in good yields. The procedure is compatible with a range of thiols and disulfides and may be amenable for preparing a wide range of thioglycosides with various glycons and aglycons. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.12.009

文献信息

• Nickel-Catalyzed Arylation, Alkenylation, and Alkynylation of Unprotected Thioglycosides at Room Temperature
  作者：Etienne Brachet、Jean-Daniel Brion、Mouad Alami、Samir Messaoudi

  DOI：10.1002/chem.201302999

  日期：2013.11.4

  Unprotected thioglycosides were effective nucleophiles for Ni0‐catalyzed CS bond‐forming reaction with functionalized (hetero)aryl, alkenyl, and alkynyl halides. The functional‐group tolerance on the electrophilic partner was typically high and the anomeric selectivities of the thioglycosides were high in all cases. The efficiency of this general procedure was well‐demonstrated by the synthesis of

  未保护的硫代糖苷是Ni 0催化的CS键与官能化的（杂）芳基，烯基和炔基卤化物反应的有效亲核试剂。在所有情况下，对亲电子分子的官能团耐受性通常都很高，硫代糖苷的端基异构体选择性也很高。合成4-甲基-7-硫代伞形酮基-β- D-纤维二糖苷（MUS-CB）很好地证明了这种通用程序的效率。