1,2:5,6-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucofuranose | 31843-56-8

• 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-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucofuranose
• 英文别名: [(2R,3R,4S,5R,6S)-6-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 31843-56-8
• 化学式: C₂₆H₃₈O₁₅
• 分子量: 590.579
• InChiKey: NOQQDZFWDIAZSB-MEGZDARUSA-N

物化性质

• 沸点：
  596.4±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 4 A molecular sieve 、 copper(II) bis(trifluoromethanesulfonate) 、 甲基三辛基氯化铵 、 copper(II) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 1,2:5,6-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucofuranose
  参考文献：
  名称：

  异头磺酰亚胺的合成及其作为新的糖基供体家族的用途

  摘要：

  我们介绍了一种方便的异头磺酰亚胺合成方法，其作为糖基供体的能力已经用各种亲硫试剂和受体进行了测试。

  DOI：

  10.1002/1099-0690(20021)2002:1<171::aid-ejoc171>3.0.co;2-7

文献信息

• Synthesis of glycosides via indium(III) chloride mediated activation of glycosyl halide in neutral condition
  作者：Debaraj Mukherjee、Pradip Kumar Ray、Uday Sankar Chowdhury

  DOI：10.1016/s0040-4020(01)00699-8

  日期：2001.9

  Various glycosides and disaccharides were synthesized through coupling of glycosyl bromides with acceptors in presence of indium chloride as a promoter. Glycosidation reactions proceeded with high stereoselectivity.

  在氯化铟作为促进剂的存在下，通过将糖基溴化物与受体偶联，可以合成各种糖苷和二糖。糖苷化反应以高立体选择性进行。
• 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。
• Iodonium promoted reactions of disarmed thioglycosides
  作者：Peter Konradsson、Uko E. Udodong、Bert Fraser-Reid

  DOI：10.1016/s0040-4039(00)97609-3

  日期：1990.1
• Garegg, Per J.; Johansson, Rolf; Samuelsson, Bertil, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 4, p. 249 - 250
  作者：Garegg, Per J.、Johansson, Rolf、Samuelsson, Bertil

  DOI：——

  日期：——
• First synthesis of anomeric sulfimides - efficient glycosyl donors
  作者：Stéphanie Cassel、Isabelle Plessis、Hans Peter Wessel、Patrick Rollin

  DOI：10.1016/s0040-4039(98)01837-1

  日期：1998.10

  Sugar-derived anomeric sulfimides were prepared in high yields from the corresponding thioglycosides and their ability to act as glycosyl donors was investigated. (C) 1998 Elsevier Science Ltd. All rights reserved.