2-bromoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside | 92171-49-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside
• 英文别名: 2-bromoethyl 2',3',6',2",3",4",6"-hepta-O-acetyl-β-D-lactopyranose；2-Bromoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D-galactopyranoside；[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-(2-bromoethoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 92171-49-8
• 化学式: C₂₈H₃₉BrO₁₈
• 分子量: 743.511
• InChiKey: CHNNLAAIGGQBOC-SLIWNODJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  47
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2-bromoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside 在 sodium azide 作用下， 生成 2-azido ethyl 2',3',6',2",3",4",6"-hepta-O-acetyl-β-D-lactopyranose
  参考文献：
  名称：

  Triazole linked lower rim glycosyl appended 1,3-calix[4]arene conjugates: Synthesis, characterization, and their interaction with jacalin

  摘要：

  Triazole linked lower rim galactosyl and lactosyl appended calix[4]arene conjugates have been synthesized by 1,3 dipolar addition of glycosyl azide and calix[4]arene alkyne. All these conjugates were characterized by H-1 and C-13 NMR, IR and mass spectrometry. Interaction of amino acids with the galactosyl conjugate of calix[4]arene (5) was studied using absorption and H-1 NMR techniques. Absorption studies showed that Trp interacts with triazole ring of 5. This was further confirmed by H-1 NMR study which showed an upfield shift in the triazole proton of 5 upon titrating with Trp. The preliminary studies of interaction of these conjugates with Jacalin were demonstrated by fluorescence and circular dichroism (CD) spectroscopy techniques. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.09.010
• 作为产物：
  描述：

  、 2-溴乙醇 在 三氟化硼乙醚 作用下， 生成 2-bromoethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Triazole linked lower rim glycosyl appended 1,3-calix[4]arene conjugates: Synthesis, characterization, and their interaction with jacalin

  摘要：

  Triazole linked lower rim galactosyl and lactosyl appended calix[4]arene conjugates have been synthesized by 1,3 dipolar addition of glycosyl azide and calix[4]arene alkyne. All these conjugates were characterized by H-1 and C-13 NMR, IR and mass spectrometry. Interaction of amino acids with the galactosyl conjugate of calix[4]arene (5) was studied using absorption and H-1 NMR techniques. Absorption studies showed that Trp interacts with triazole ring of 5. This was further confirmed by H-1 NMR study which showed an upfield shift in the triazole proton of 5 upon titrating with Trp. The preliminary studies of interaction of these conjugates with Jacalin were demonstrated by fluorescence and circular dichroism (CD) spectroscopy techniques. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.09.010

文献信息

• Glycosides
  申请人：Svenska Sockerfabriks AB

  公开号：US04675392A1

  公开（公告）日：1987-06-23

  An O-glycoside having the general formula: (sugar).sub.n --O--(CH.sub.2).sub.m --Hal wherein Hal is chlorine, bromine or iodine, m is an integer of 2-20 inclusive and n is an integer of 1 to 10, inclusive, with the proviso that when n=1 and m=2, the aldose is different from glucose; An O-glycoside having the general formula: (sugar).sub.n --O--(CH.sub.2).sub.m --S--R--R' wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R' is selected from the group consisting of H, CHO, CH(OR').sub.2, NO.sub.2, NH.sub.2, OH, SH, COOH, COOCH.sub.3, COOCH.sub.2 CH.sub.3, CONHNH.sub.2 and CON.sub.3, wherein R" is C.sub.1-4 -alkyl; A glycoconjugate having the general formula: (sugar).sub.n --O--(CH.sub.2).sub.m --S--R--R" wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R" constitutes a carrier; A bi-dentate O-glycoside having the general formula: [(sugar).sub.n --O--(CH.sub.2).sub.m --S--.sub.2 R wherein m, n and R have the above meaning; and processes for their preparation.

  一种具有一般式的O-糖苷：(糖).sub.n --O--(CH.sub.2).sub.m --Hal，其中Hal为氯、溴或碘，m为2-20的整数，n为1-10的整数，但当n=1且m=2时，醛糖与葡萄糖不同；一种具有一般式的O-糖苷：(糖).sub.n --O--(CH.sub.2).sub.m --S--R--R'，其中n为1-10的整数，m为2-20的整数，R选自最多具有25个碳原子的烷基和芳基，R'选自H、CHO、CH(OR').sub.2、NO.sub.2、NH.sub.2、OH、SH、COOH、COOCH.sub.3、COOCH.sub.2 CH.sub.3、CONHNH.sub.2和CON.sub.3的群，其中R"为C.sub.1-4-烷基；一种具有一般式的糖基结合物：(糖).sub.n --O--(CH.sub.2).sub.m --S--R--R"，其中n为1-10的整数，m为2-20的整数，R选自最多具有25个碳原子的烷基和芳基，R"构成载体；一种具有一般式的双叉O-糖苷：[(糖).sub.n --O--(CH.sub.2).sub.m --S--.sub.2R其中m，n和R具有上述含义；以及它们的制备过程。
• New and novel glycosides, glycoconjugates and processes for their preparation
  申请人：BIOCARB AB

  公开号：EP0098252A2

  公开（公告）日：1984-01-11

  An O-glycoside having the general formula: wherein Hal is chlorine, bromine or iodine, m is an integer of 2-20 inclusive and n is an integer of 1 to 10, inclusive, with the proviso that when n = 1 and m = 2, the aldose is different from glucose; An O-glycoside having the general formula: wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R' is selected from the group consisting of H, CHO, CH(OR")2, NO2, NH2, OH, SH, COOH, COOCH3, COOCH2CH3, CONHNH2 and CON3, wherein R" is C1-4-alkyl; A glycoconjugate having the general formula: wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R" constitutes a carrier; A bi-dentate 0-glycoside having the general formula: wherein m, n and R have the above meaning; and processes for their preparation.

  具有通式的 O-糖苷： 其中 Hal 为氯、溴或碘，m 为 2-20 个整数（含），n 为 1-10 个整数（含），但当 n = 1 和 m = 2 时，醛糖不同于葡萄糖； 具有通式的 O-糖苷： 其中 n 为 1-10 个整数（含 1-10 个），m 为 2-20 个整数（含 2-20 个），R 选自具有至多 25 个碳原子的烷基和芳基组成的组，R'选自 H、CHO、CH(OR")2、NO2、NH2、OH、SH、COOH、COOCH3、COOCH2CH3、CONHNH2 和 CON3 组成的组，其中 R "为 C1-4 烷基； 具有通式的糖结合剂： 其中 n 为 1-10 个整数（含 1-10 个），m 为 2-20 个整数（含 2-20 个），R 选自具有最多 25 个碳原子的烷基和芳基组成的组，R" 构成载体； 具有通式的双齿 0-糖苷： 其中 m、n 和 R 具有上述含义；及其制备方法。
• 2-Bromoethyl glycosides: applications in the synthesis of spacer-arm glycosides
  作者：Jan Dahmén、Torbjörn Frejd、Gunnar Grönberg、Thomas Lave、Göran Magnusson、Ghazi Noori

  DOI：10.1016/0008-6215(83)88059-8

  日期：1983.7
• US4675392A
  申请人：——

  公开号：US4675392A

  公开（公告）日：1987-06-23