methyl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxofuranoside | 63087-95-6

• 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 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxofuranoside
• 英文别名: methyl-2,3-O-isopropylidene-5-O-p-toluenesulfonyl-α-L-lyxofuranoside；[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-methylbenzenesulfonate
• CAS: 63087-95-6
• 化学式: C₁₆H₂₂O₇S
• 分子量: 358.412
• InChiKey: IAPMZKRZMYQZSW-QPSCCSFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxofuranoside 在 盐酸 、 硫酸 、 sodium 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 methyl 5-thio-α-D-lyxopyranoside
  参考文献：
  名称：

  5-硫代-d-阿拉伯糖和5-硫代-d-木糖的合成及其甲基吡喃糖苷

  摘要：

  摘要1,2-O-异亚丙基-5-O-甲苯基-对-磺酰基-β-d-阿拉伯呋喃糖已通过3-O-乙酰基-5-S-乙酰基-1转化为5-硫代-d-阿拉伯糖， 2-O-异亚丙基-5-硫代-β-d-呋喃糖。类似地，由甲基2，3-O-异亚丙基-5-O-甲磺酰基（或甲苯-对-磺酰基）-α-d-呋喃呋喃糖苷经由5-S-乙酰基（或苯甲酰基）甲基获得5-噻吩基-二糖。 -1,2-O-异亚丙基-5-硫代-α-d-呋喃呋喃糖苷。通过游离糖或上述硫代酯中间体的甲醇分解获得相应的甲基硫代吡喃糖苷。现在已经知道所有的5-硫代-d-戊吡喃糖及其甲基的5-硫代-d-戊吡喃糖苷，并且总结了它们的一些特性。

  DOI：

  10.1016/0008-6215(85)85213-7
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-α-D-lyxofuranoside 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 8.0h， 以96%的产率得到methyl 2,3-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-lyxofuranoside
  参考文献：
  名称：

  Bicyclic azasugars containing a glycosidic heteroatom 2: D-lyxose analogues

  摘要：

  Bicyclic azasugar analogues of D-lyxose containing a glycosidic heteroatom that is O, N, or S have been prepared from 5-O-tosyl-D-lyxose and characterized by NMR spectroscopy. The nitrogen analogue has an overwhelming preference to be the beta-anomer, but the oxygen and sulfur compounds exist as mixtures of anomers with the alpha-anomer predominating in the latter case. The alpha-anomers undergo conformational equilibration with the sulfur analogue being fast at room temperature but the oxygen compound requiring 60 degrees C to achieve fast exchange and a sharply resolved H-1 NMR spectrum at 500 MHz. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00901-1

文献信息

• Enzyme Fingerprints of Activity, and Stereo- and Enantioselectivity from Fluorogenic and Chromogenic Substrate Arrays
  作者：Denis Wahler、Fabrizio Badalassi、Paolo Crotti、Jean-Louis Reymond

  DOI：10.1002/1521-3765(20020715)8:14<3211::aid-chem3211>3.0.co;2-g

  日期：2002.7.15

  A series of stereochemically and structurally diverse fluorogenic and chromogenic substrates for hydrolytic enzymes has been synthesized and used to characterize enzyme activity profiles of esterases, lipases, proteases, peptidases, phosphatases, and epoxide hydrolases. The substrates used are particularly resilient to nonspecific reactions due to their mechanism of activation. The activities recorded with the individual substrates are therefore remarkably reproducible, and enable us to use the overall pattern of activity as a specific fingerprint for the enzyme sample. Fingerprints of activity, and enantio- and stereoselectivity are displayed as arrays of color-scale squares that are easily analyzed visually. Such fingerprints might be useful for quality control, enzyme discovery, and possibly for addressing the issue of functional convergence in enzymes.
• Identification of the 5-Methylthiopentosyl Substituent inMycobacterium tuberculosis Lipoarabinomannan
  作者：W. Bruce Turnbull、Kazumi Hiruma Shimizu、Delphi Chatterjee、Steve W. Homans、Achim Treumann

  DOI：10.1002/anie.200454119

  日期：2004.7.26
• [EN] MONOSACCHARIDE DERIVATIVES<br/>[FR] DERIVES DU MONOSACCHARIDE
  申请人：RANBAXY LAB LTD

  公开号：WO2005100373A2

  公开（公告）日：2005-10-27

  The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies, including inflammatory and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis or allergic rhinitis. Pharmacological compositions containing the compounds of the present invention and the methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, type I diabetes, psoriasis, allograft rejection, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis or allergic rhinitis and other inflammatory and/or autoimmune disorders, using the compounds are also provided.
• Synthesis of 5-thio-d-arabinose and 5-thio-d-lyxose and their methyl glycopyranosides
  作者：Neil A. Hughes、Namboole M. Munkombwe

  DOI：10.1016/0008-6215(85)85213-7

  日期：1985.2

  Abstract 1,2- O -Isopropylidene-5- O -toluene- p -sulphonyl-β- d -arabinofuranose has been converted into 5-thio- d -arabinose via 3- O -acetyl-5- S -acetyl-1,2- O -isopropylidene-5-thio-β- d -arabinofuranose. 5-Thio- d -lyxose was similarly obtained from methyl 2,3- O -isopropylidene-5- O -methanesulphonyl(or toluene- p -sulphonyl)-α- d -lyxofuranoside via methyl 5- S -acetyl(or benzoyl)-1,2- O -

  摘要1,2-O-异亚丙基-5-O-甲苯基-对-磺酰基-β-d-阿拉伯呋喃糖已通过3-O-乙酰基-5-S-乙酰基-1转化为5-硫代-d-阿拉伯糖， 2-O-异亚丙基-5-硫代-β-d-呋喃糖。类似地，由甲基2，3-O-异亚丙基-5-O-甲磺酰基（或甲苯-对-磺酰基）-α-d-呋喃呋喃糖苷经由5-S-乙酰基（或苯甲酰基）甲基获得5-噻吩基-二糖。 -1,2-O-异亚丙基-5-硫代-α-d-呋喃呋喃糖苷。通过游离糖或上述硫代酯中间体的甲醇分解获得相应的甲基硫代吡喃糖苷。现在已经知道所有的5-硫代-d-戊吡喃糖及其甲基的5-硫代-d-戊吡喃糖苷，并且总结了它们的一些特性。
• Bicyclic azasugars containing a glycosidic heteroatom 2: D-lyxose analogues
  作者：David A. Berges、Na Zhang、Liwu Hong

  DOI：10.1016/s0040-4020(99)00901-1

  日期：1999.12

  Bicyclic azasugar analogues of D-lyxose containing a glycosidic heteroatom that is O, N, or S have been prepared from 5-O-tosyl-D-lyxose and characterized by NMR spectroscopy. The nitrogen analogue has an overwhelming preference to be the beta-anomer, but the oxygen and sulfur compounds exist as mixtures of anomers with the alpha-anomer predominating in the latter case. The alpha-anomers undergo conformational equilibration with the sulfur analogue being fast at room temperature but the oxygen compound requiring 60 degrees C to achieve fast exchange and a sharply resolved H-1 NMR spectrum at 500 MHz. (C) 1999 Elsevier Science Ltd. All rights reserved.