methyl 3,4-O-isopropylidene-6-O-tosyl-β-D-galactopyranoside | 20688-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3,4-O-isopropylidene-6-O-tosyl-β-D-galactopyranoside
• 英文别名: ((3aS,4R,6R,7R,7aR)-7-Hydroxy-6-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-4-yl)methyl 4-methylbenzenesulfonate；[(3aS,4R,6R,7R,7aR)-7-hydroxy-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 20688-91-9
• 化学式: C₁₇H₂₄O₈S
• 分子量: 388.439
• InChiKey: XCYNJCRDVMCBCG-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3,4-O-isopropylidene-6-O-tosyl-β-D-galactopyranoside 在 吡啶 、 盐酸 、 ruthenium trichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 iodonium di(2,4,6-collidinium) triflate 、 4 A molecular sieve 、 硫酸 、 potassium tert-butylate 、 四丁基碘化铵 、 sodium hydride 、 tetrabutylammonium borohydride 、 溶剂黄146 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 54.4h， 生成 allyl 3-O-(3,6-dideoxy-α-D-xylo-hexapyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Preparation of Disaccharide Haptens Corresponding toSalmonellaSerogroups B and D

  摘要：

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.

  DOI：

  10.1080/07328309608005684
• 作为产物：
  描述：

  对甲苯磺酰氯 、 methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 在 吡啶 作用下， 以70%的产率得到methyl 3,4-O-isopropylidene-6-O-tosyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells

  摘要：

  A series of carbamides derived from 1,2:5,6-di-O-isopropylidene-D-gluco- (1) and D-allofuranose (3) as well as their 5,6-O-deprotected analogues (2 and 4) and methyl 3,4-O-isopropylidene-alpha- and beta-D-galactopyranosides (5 and 6) have been prepared in order to evaluate their ability to induce erythroid differentiation of human erythroleukemic K562 cells. Twenty out of 51 carbamides tested exhibit an appreciable activity as inducers of erythroid differentiation and have been fully characterized and described. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.05.001

文献信息

• Oxy-imino saccharidic derivatives as a new structural class of aldose reductase inhibitors endowed with anti-oxidant activity
  作者：Felicia D'Andrea、Stefania Sartini、Ilaria Piano、Matteo Franceschi、Luca Quattrini、Lorenzo Guazzelli、Lidia Ciccone、Elisabetta Orlandini、Claudia Gargini、Concettina La Motta、Susanna Nencetti

  DOI：10.1080/14756366.2020.1763331

  日期：2020.1.1

  Aldose reductase is a key enzyme in the development of long term diabetic complications and its inhibition represents a viable therapeutic solution for people affected by these pathologies. Therefore, the search for effective aldose reductase inhibitors is a timely and pressing challenge. Herein we describe the access to a novel class of oxyimino derivatives, obtained by reaction of a 1,5-dicarbonyl substrate

  醛糖还原酶是长期糖尿病并发症发展中的关键酶，其抑制作用为受这些病理影响的人提供了可行的治疗方案。因此，寻找有效的醛糖还原酶抑制剂是一个及时而紧迫的挑战。在本文中，我们描述了通过1,5-二羰基底物与O-（芳基甲基）羟胺反应获得的一类新型的氧亚氨基衍生物。已证明合成的化合物对目标酶具有活性。当在由暴露于高糖培养基的感光受体样661w细胞系制成的糖尿病性视网膜病变的体外模型中测试时，性能最好的抑制剂化合物（Z）-8还可降低细胞死亡和凋亡过程。高血糖症引发的压力。
• Jacobsen, Steffen; Mols, Ole, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 3, p. 163 - 168
  作者：Jacobsen, Steffen、Mols, Ole

  DOI：——

  日期：——
• A sugar aminoacid for the development of multivalent ligands for Escherichia coli 0157 verotoxin
  作者：Darren Gibson、Steven W. Homans、Robert A. Field

  DOI：10.1016/j.tetasy.2009.02.021

  日期：2009.5

  Functionalised carbohydrates for incorporation into multivalent ligands for the Escherichia coli O157 verotoxin are highly desirable. Here, we report the synthesis of a sugar aminoacid based on the known Gal-alpha-1,4-Gal ligand for verotoxin in eight steps and in similar to 10% overall yield. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells
  作者：Martina Landi、Giorgio Catelani、Felicia D'Andrea、Eleonora Ghidini、Gabriele Amari、Puccini Paola、Nicoletta Bianchi、Roberto Gambari

  DOI：10.1016/j.ejmech.2008.05.001

  日期：2009.2

  A series of carbamides derived from 1,2:5,6-di-O-isopropylidene-D-gluco- (1) and D-allofuranose (3) as well as their 5,6-O-deprotected analogues (2 and 4) and methyl 3,4-O-isopropylidene-alpha- and beta-D-galactopyranosides (5 and 6) have been prepared in order to evaluate their ability to induce erythroid differentiation of human erythroleukemic K562 cells. Twenty out of 51 carbamides tested exhibit an appreciable activity as inducers of erythroid differentiation and have been fully characterized and described. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Preparation of Disaccharide Haptens Corresponding to<i>Salmonella</i>Serogroups B and D
  作者：Korien Zegelaar-Jaarsveld、Simon C. van der Plas、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1080/07328309608005684

  日期：1996.8

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.