1,2:5,6-di-O-isopropylidene-3-O-(β-D-glycopyranosyl)-D-glucofuranose | 80264-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-O-(β-D-glycopyranosyl)-D-glucofuranose
• CAS: 80264-91-1
• 化学式: C₁₈H₃₀O₁₁
• 分子量: 422.43
• InChiKey: LCINONQSROIXFC-ZRIWIVTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  145.53
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-(β-D-glycopyranosyl)-D-glucofuranose 在 sodium tetrahydroborate 、 硫酸 作用下， 以 水 为溶剂， 反应 27.5h， 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-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucofuranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到1,2:5,6-di-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

文献信息

• Reaction of some D-glucobioses with 2,2-dimethoxypropane
  作者：Yoshimitsu Ueno、Kohsuke Hori、Ryo Yamauchi、Makoto Kiso、Akira Hasegawa、Koji Kato

  DOI：10.1016/s0008-6215(00)84695-9

  日期：1981.10

  Abstract Laminarabiose, cellobiose, and gentiobiose were acetonated with 2,2-dimethoxy-propane under various conditions. Two isopropylidene acetals in which the reducing D -glucose residue had the furanoid form were obtained from laminarabiose, and two, in which the reducing D -glucose residue formed the acyclic dimethyl acetal, from cellobiose. Gentiobiose gave both types of isopropylidene compound

  摘要在不同条件下，用2,2-二甲氧基丙烷对拉米纳糖，纤维二糖和龙胆二糖进行了乙酰化。从纤维二糖获得了两个还原亚丙基缩醛具有呋喃形式的异亚丙基缩醛，和两个从纤维二糖还原亚基缩醛形成了无环二甲基缩醛的缩二醛。龙胆二糖给出了两种类型的异亚丙基化合物。