1,2-O-isopropylidene-3-O-(β-D-glycopyranosyl)-D-glucofuranose | 794591-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3-O-(β-D-glycopyranosyl)-D-glucofuranose
• CAS: 794591-48-3
• 化学式: C₁₅H₂₆O₁₁
• 分子量: 382.365
• InChiKey: WYTDWXLNCHZMSK-CXIHMHBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  167.53
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-O-(β-D-glycopyranosyl)-D-glucofuranose 在 sodium tetrahydroborate 、 硫酸 作用下， 以 水 为溶剂， 反应 3.5h， 生成 3-O-(β-D-glucopyranosyl)-D-glucitol
  参考文献：
  名称：

  Two approaches to the synthesis of 3-β-d-glucopyranosyl-d-glucitol

  摘要：

  Glycosidation of 1,2:5,6-di-O-isopropylidene-D-glucose with tetra-O-acetyl-glucosyl bromide in 1:1 benzene-MeNO2 afforded approximately equal amounts of the 3-O-beta-D-glycoside and the rearranged 6-O-beta-D-glycoside, while in MeCN only the latter was formed. When tetra-O-acetyl-beta-thiophenylgiucoside was used as donor in CH2Cl2 in the presence of NIS/TfOH as activator, the 6-O-beta-D-glycoside and a 3-O-orthoester were formed in a 1:2 ratio at -20 degreesC, while at 20 degreesC only the former could be isolated. Glycosidation of 1-O-benzoyl-2,4-0-benzylidene-5,6-O-isopropylidene-D-glycutol with tetra-O-acetyl-glucosyl bromide in MeCN in the presence of Hg(CN)(2) afforded the corresponding 3-O-alpha- and 3-O-beta-glycopyranoside in a 1:4 ratio in MeCN and 1:5 in 1:1 benzene-MeNO2. respectively. When Hg(CN)(2)/HgBr2 was used as promoter, the corresponding orthoester was also formed. When tetra-O-acetyl-beta-thiophenylglucoside was used as donor, the 3-O-beta-anomer and the orthoester were obtained predominantly in a 3:2 ratio together with traces of the 3-O-alpha-glycoside. Both beta-glycosides could be smoothly converted into 3-beta-D-glucopyranosyl-D-glucitol (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.019
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-(β-D-glycopyranosyl)-D-glucofuranose 在 硫酸 作用下， 反应 24.0h， 以92%的产率得到1,2-O-isopropylidene-3-O-(β-D-glycopyranosyl)-D-glucofuranose
  参考文献：
  名称：

  Two approaches to the synthesis of 3-β-d-glucopyranosyl-d-glucitol

  摘要：

  Glycosidation of 1,2:5,6-di-O-isopropylidene-D-glucose with tetra-O-acetyl-glucosyl bromide in 1:1 benzene-MeNO2 afforded approximately equal amounts of the 3-O-beta-D-glycoside and the rearranged 6-O-beta-D-glycoside, while in MeCN only the latter was formed. When tetra-O-acetyl-beta-thiophenylgiucoside was used as donor in CH2Cl2 in the presence of NIS/TfOH as activator, the 6-O-beta-D-glycoside and a 3-O-orthoester were formed in a 1:2 ratio at -20 degreesC, while at 20 degreesC only the former could be isolated. Glycosidation of 1-O-benzoyl-2,4-0-benzylidene-5,6-O-isopropylidene-D-glycutol with tetra-O-acetyl-glucosyl bromide in MeCN in the presence of Hg(CN)(2) afforded the corresponding 3-O-alpha- and 3-O-beta-glycopyranoside in a 1:4 ratio in MeCN and 1:5 in 1:1 benzene-MeNO2. respectively. When Hg(CN)(2)/HgBr2 was used as promoter, the corresponding orthoester was also formed. When tetra-O-acetyl-beta-thiophenylglucoside was used as donor, the 3-O-beta-anomer and the orthoester were obtained predominantly in a 3:2 ratio together with traces of the 3-O-alpha-glycoside. Both beta-glycosides could be smoothly converted into 3-beta-D-glucopyranosyl-D-glucitol (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.019