(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-(1→1)-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside | 1167993-89-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-(1→1)-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: 2,3,4-tri-O-acetyl-β-L-fucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]sulfanyloxan-2-yl]methyl acetate
• CAS: 1167993-89-6
• 化学式: C₂₆H₃₆O₁₆S
• 分子量: 636.628
• InChiKey: QNVIVESNMLRUEC-FTWZNCSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  228
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-6-脱氧-alpha-L-溴代半乳糖 在 二硫化碳 、 sodiumsulfide nonahydrate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 生成 (2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-(1→1)-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of β-Glycosyl Thiols and Their Synthetic Applications

  摘要：

  A significantly fast reaction condition for the exclusive preparation beta-glycosyl thiol derivatives has been developed successfully. The reaction condition is one-step, fast, high yielding, highly stereoselective, and requires only benchtop chemicals. Further reaction of glycosyl thiol derivatives with Michael acceptors and alkylating agents furnished thioglycosides and (1,1)-thiolinked trehalose analogs.

  DOI：

  10.1021/jo302115k

文献信息

• A facile preparation of trehalose analogues: 1,1-thiodisaccharides
  作者：Goreti Ribeiro Morais、Andrew J. Humphrey、Robert A. Falconer

  DOI：10.1016/j.carres.2009.03.017

  日期：2009.5

  The synthesis of 1,1-thiodisaccharide trehalose analogues in good to excellent yields by a Lewis acid (BF3 center dot Et2O)-catalysed coupling of sugar per-O-acetate with thiosugar is described. The reactivity of different sugar per-O-acetates and thiosugars is explored. (C) 2009 Elsevier Ltd. All rights reserved.