1,6-anhydro-3,4-O-isopropylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranose | 83441-58-1

• 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: 1,6-anhydro-3,4-O-isopropylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(1R,2S,6S,7R,8R)-4,4-dimethyl-3,5,9,11-tetraoxatricyclo[6.2.1.02,6]undecan-7-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 83441-58-1
• 化学式: C₂₃H₃₂O₁₄
• 分子量: 532.499
• InChiKey: VKXDIBLMYDLFBJ-SYHNZQHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  161
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-3,4-O-isopropylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranose 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以78%的产率得到[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(1R,2R,3S,4R,5R)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl]oxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis of α-Glycosyl Thiols by Stereospecific Ring-Opening of 1,6-Anhydrosugars

  摘要：

  Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of a-glycosyl thiols. All the reactions were highly stereoselective and afforded the a-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding a-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to a-glycosyl thiols of great value was established.

  DOI：

  10.1021/jo202069y
• 作为产物：
  描述：

  1,6-anhydro-3,4-O-isopropylidene-β-D-galactopyranose 在 4-二甲氨基吡啶 、 降钙素杂质10 、 trityl tetrafluoroborate 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 73.8h， 生成 1,6-anhydro-3,4-O-isopropylidene-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranose
  参考文献：
  名称：

  乙酰化的外和​​内氰基亚乙基衍生物在糖基化反应中的不同反应性

  摘要：

  摘要具有d-葡萄糖，d-木糖和d-半乳糖构型（2-6）与伯（8）和仲（9）三苯甲基衍生物的乙酰化1-（内氰基）亚乙基衍生物的缩合反应较多。比相应的exo-异构体快。反应性的差异是根据构象差异来解释的。

  DOI：

  10.1016/0008-6215(89)85016-5

文献信息

• VICENT, CRISTINA;COTERON, JOSE-MIGUEL;JIMENEZ-BARBERO, JESUS;MARTIN-LOMAS+, CARBOHYDR. RES., 194,(1989) C. 163-169
  作者：VICENT, CRISTINA、COTERON, JOSE-MIGUEL、JIMENEZ-BARBERO, JESUS、MARTIN-LOMAS+

  DOI：——

  日期：——