2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-galactopyranosyl bromide | 69349-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-galactopyranosyl bromide
• 英文别名: Gal2Ac3Ac4Ac6Ac(a1-4)a-Gal1Br2Ac3Ac6Ac；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 69349-74-2
• 化学式: C₂₆H₃₅BrO₁₇
• 分子量: 699.458
• InChiKey: NLFHLQWXGDPOME-ZEWMEEHZSA-N

物化性质

• 沸点：
  659.5±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-galactopyranosyl bromide 生成 [(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-(2,3,4,5,6-pentachlorophenoxy)-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  KUDZUXARA, XIROMI;FUDZIMAKI, ITSUO

  摘要：

  DOI：

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是氯、溴或碘，m是2-20的整数，n是1到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是1-10的整数，m是2-20的整数，R选自最多含有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，其中R"是C.sub.1-4-烷基；一种具有一般式的糖共轭物：(糖).sub.n --O--(CH.sub.2).sub.m --S--R--R"，其中n是1-10的整数，m是2-20的整数，R选自最多含有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.2 R，其中m、n和R具有上述含义；以及它们的制备方法。
• Synthesis of spacer-arm, lipid, and ethyl glycosides of the trisaccharide portion [α-d-Gal-(1→4)-β-d-Gal-(1→4)-β-d-Glc] of the blood-group Pk antigen: Preparation of neoglycoproteins
  作者：Jan Dahmén、Torbjörn Frejd、Göran Magnusson、Ghazi Noori、Anne-Sofie Carlström

  DOI：10.1016/0008-6215(84)85102-2

  日期：1984.4

  Abstract The title compounds were prepared via the acetylated 2-bromoethyl glycoside 11 of α- d -Gal-(1→4)-β- d -Gal-(1→4)-β- d -Glc by displacement of bromide ion with methyl 3-mercaptopropionate, octadecanethiol, and hydrogen, respectively. Silver triflate-promoted glycosylation of 2-bromoethyl 2,3,6-tri-O-benzyl-β- d -glucopyranoside with 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α- d -galactopyranosyl)-α-

  摘要通过α-d-Gal-（1→4）-β-d-Gal-（1→4）-β-d-Glc的乙酰化2-溴乙基糖苷11置换溴离子来制备标题化合物。 3-巯基丙酸甲酯，十八烷硫醇和氢。三氟甲磺酸银促进的2,3,6-三-O-乙酰基-4-O-（2,3,4,2-溴乙基2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷的糖基化6-四-O-乙酰基-α-d-吡喃半乳糖基溴）-α-d-吡喃半乳糖基溴得到11。通过基本上相同的途径制备了11的四氘代类似物。由3-巯基丙酸甲酯形成的间隔臂糖苷与牛血清白蛋白和匙孔血蓝蛋白偶联。
• Synthesis of spacer-arm, lipid, and ethyl glycosides of the terminal trisaccharide [α-d-Gal-(1→4)-β-d-Gal-(1→4)-β-d-GlcNAc] portion of the blood-group P1 antigen: Preparation of neoglycoproteins
  作者：Jan Dahmén、Torbjörn Frejd、Göran Magnusson、Ghazi Noori、Anne-Sofie Carlström

  DOI：10.1016/0008-6215(84)85299-4

  日期：1984.7

  Abstract The title compounds were prepared via the acetylated 2-bromoethyl β-glycoside ( 5 ) of α- d -Gal-(1→4)-β- d -Gal-(1→4)-β- d -GlcNAc by displacement of bromide ion with methyl 3-mercaptopropionate, octadecanethiol, and hydrogen, respectively. Silver triflate-promoted glycosylation of 2-bromoethyl 3,6-di- O -benzyl-2-deoxy-2-phthalimido-β- d -glucopyranoside with 2,3,6-tri- O -acetyl-4- O -(2

  摘要通过α-d-Gal-（1→4）-β-d-Gal-（1→4）-β-d-GlcNAc的乙酰化2-溴乙基β-糖苷（5）制备标题化合物分别与3-巯基丙酸甲酯，十八烷硫醇和氢形成溴离子。三氟甲磺酸银促进的2,3,6-三-O-乙酰基-4-O-（2-溴乙基3,6-二-O-苄基-2-脱氧-2-邻苯二甲酰亚胺-β-d-吡喃葡萄糖苷的糖基化作用2,3,4,6-四-O-乙酰基-α-d-半乳糖吡喃糖基）-α-d-半乳糖基吡喃糖基溴得到5。将衍生自3-巯基丙酸甲酯的间隔臂糖苷与牛血清白蛋白和匙孔血蓝蛋白偶联，得到新糖蛋白。
• Nilsson, Ulf; Johansson, Roger; Magnusson, Goeran, Chemistry - A European Journal, 1996, vol. 2, # 3, p. 295 - 302
  作者：Nilsson, Ulf、Johansson, Roger、Magnusson, Goeran

  DOI：——

  日期：——
• 2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars
  作者：Karl Jansson、Stefan Ahlfors、Torbjoern Frejd、Jan Kihlberg、Goeran Magnusson、Jan Dahmen、Ghazi Noori、Kristina Stenvall

  DOI：10.1021/jo00259a006

  日期：1988.11