ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside | 224047-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside
• 英文别名: 1-ethylsulfenyl-1,2-dideoxy-2-N-tetrachlorophthalimido-β-D-glucopyranoside；4,5,6,7-tetrachloro-2-[(2S,3R,4R,5S,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 224047-33-0
• 化学式: C₁₆H₁₅Cl₄NO₆S
• 分子量: 491.176
• InChiKey: LJNLDPHJHHEVFL-HOSATFPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside 在 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 三丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 23.75h， 生成 ethyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  EFFICIENT SYNTHESIS OF POLYLACTOSAMINE STRUCTURES THROUGH REGIOSELECTIVE GLYCOSYLATIONS1

  摘要：

  Di-, tri- and tetramers of beta-(1 -->3)-linked N-acetyllactosamine residues have been synthesised as their methyl glycosides, to be used in ITC binding studies to various galectins. The synthetic strategy involves two types of regioselective glycosylations: couplings of a galactosyl donor to 3,4-diol N-tetrachlorophthalimido glucose acceptors to give the lactosamine monomer building blocks, and subsequent formation of the oligomers through consecutive couplings of lactosamine donors to 2',3',4'-lactosamine acceptors, with high selectivity for the desired products.

  DOI：

  10.1081/car-100108275
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-α-D-glucopyranosyl bromide 在 盐酸 、 silver zeolite 、 水 、 四氯化钛 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Access to tetrachlorophthalimide-protected ethyl 2-amino-2-deoxy-1-thio-β-d-glucopyranosides

  摘要：

  Ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-beta-D-glucopyranoside (7) was prepared from glucosamine hydrochloride in four steps with a 20-25% overall yield. Formation of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (5) was found to be crucial for this reaction sequence since the corresponding alpha-1-acetate did not react in Lewis-acid-catalyzed ethylthio glycosidations. Formation of the beta-1-acetate (5) was achieved by treatment of 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-alpha-D-glucopyranosol bromide(4) with acetic acid under silver zeolite promotion. This was necessary because conditions normally used for p-l-acetate formation were not tolerated by the tetrachlorophthalimido (TCP) group. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00309-7

文献信息

• Highly Diastereoselective Oxidation of 2-Amino-2-deoxy-1-thio-β-<scp>d</scp>-glucopyranosides:  Synthesis of Imino Sulfinylglycosides
  作者：Noureddine Khiar、Inmaculada Fernández、Cristina S. Araújo、José-Antonio Rodríguez、Belén Suárez、Eleuterio Álvarez

  DOI：10.1021/jo026519q

  日期：2003.2.1

  A synthetic route to imino thioglycosides and to imino sulfinylglycosides has been developed. A detailed study on the diastereoselective oxidation of 2-amino-2-deoxy-1-thio-beta-D-glucopyranosides is reported. It has been shown that the stereochemical outcome of the oxidation is highly dependent on the protective group of the amine function. While the oxidation of iminothioglycosides is slightly diastereoselective (up to 30% de in favor of the R-S sulfoxide), a single isomer is obtained in the case of tetrachloroplithalimido derivatives. The absolute configuration of the sulfinyl glycoside was ascertained by NMR analysis using our recent model on the basis of the exo-anomeric effect corroborated by X-ray crystallography.
• EFFICIENT SYNTHESIS OF POLYLACTOSAMINE STRUCTURES THROUGH REGIOSELECTIVE GLYCOSYLATIONS1
  作者：Therese Buskas、Peter Konradsson、Stefan Oscarson

  DOI：10.1081/car-100108275

  日期：——

  Di-, tri- and tetramers of beta-(1 -->3)-linked N-acetyllactosamine residues have been synthesised as their methyl glycosides, to be used in ITC binding studies to various galectins. The synthetic strategy involves two types of regioselective glycosylations: couplings of a galactosyl donor to 3,4-diol N-tetrachlorophthalimido glucose acceptors to give the lactosamine monomer building blocks, and subsequent formation of the oligomers through consecutive couplings of lactosamine donors to 2',3',4'-lactosamine acceptors, with high selectivity for the desired products.
• Access to tetrachlorophthalimide-protected ethyl 2-amino-2-deoxy-1-thio-β-d-glucopyranosides
  作者：Lars Olsson、Sandra Kelberlau、Zhaozhong J. Jia、Bert Fraser-Reid

  DOI：10.1016/s0008-6215(98)00309-7

  日期：1998.12

  Ethyl 2-deoxy-2-tetrachlorophthalimido-1-thio-beta-D-glucopyranoside (7) was prepared from glucosamine hydrochloride in four steps with a 20-25% overall yield. Formation of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-beta-D-glucopyranoside (5) was found to be crucial for this reaction sequence since the corresponding alpha-1-acetate did not react in Lewis-acid-catalyzed ethylthio glycosidations. Formation of the beta-1-acetate (5) was achieved by treatment of 3,4,6-tri-O-acetyl-2-deoxy-2-tetrachlorophthalimido-alpha-D-glucopyranosol bromide(4) with acetic acid under silver zeolite promotion. This was necessary because conditions normally used for p-l-acetate formation were not tolerated by the tetrachlorophthalimido (TCP) group. (C) 1998 Elsevier Science Ltd. All rights reserved.