methyl 3,6-anhydro-4-O-β-D-galactopyranosyl-α-D-galactopyranoside | 19146-25-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-anhydro-4-O-β-D-galactopyranosyl-α-D-galactopyranoside
• 英文别名: Methyl 3,6-anhydro-4-O-α-D-galactopyranosyl-β-D-galactopyranoside；(2S,3R,4S,5R,6R)-2-[[(1R,3S,4R,5R,8S)-4-hydroxy-3-methoxy-2,6-dioxabicyclo[3.2.1]octan-8-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 19146-25-9
• 化学式: C₁₃H₂₂O₁₀
• 分子量: 338.312
• InChiKey: TULXNGMSCFHMKM-IYQPGZRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  147
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  甲基3,6-脱水-ALPHA-D-半乳糖苷 在 palladium on activated charcoal barium hydroxide octahydrate 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 氰化汞 、 barium(II) oxide 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 48.75h， 生成 methyl 3,6-anhydro-4-O-β-D-galactopyranosyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and conformational studies of carrabiose and its 4′-sulphate and 2,4′-disulphate

  摘要：

  Methyl alpha-carrabioside (13), and its 4-sulphate (19) and 2,4-disulphate (20) have been synthesised via glycosylation of methyl 3,6-anhydro-2-O-benzyl-alpha-D-galactopyranoside with 2,3,6-tri-O-acetyl-4-O-benzyl-beta-D-galactopyranosyl bromide and subsequent partial or complete debenzylation, sulphation, and deprotection of the resulting disaccharide derivatives. Conformational studies have been carried out on 13, 19, and 20 on the basis of 1D and 2D 1H-n.m.r. spectroscopy and molecular mechanics calculations.

  DOI：

  10.1016/0008-6215(90)80087-j

文献信息

• Efficient and stereoselective synthesis of methyl 3-O-(3,6-anhydro-β-d-galactopyranosyl)-α-d-galactopyranoside and methyl 3,6-anhydro-4-O-β-d-galactopyranosyl-α-d-galactopyranoside
  作者：Abdul Rashid、William Mackie

  DOI：10.1016/0008-6215(92)80013-q

  日期：1992.1

  Abstract Methyl 3-O-(3,6-anhydr-β- d -galactopyranosyl)-α- d -galactopyranoside (3) and methyl 3,6-anhydro-4-O-β d -galactopyranosyl-α- d -galactopyranoside (4) have been synthesised stereoselectivity using three coupling procedures. Acceptable yields were achieved using acetylated derivatives as donors and trimethylsilyl triflate as the catalyst. Intramolecular tosylate displacement to form 3,6-anhydro

  摘要甲基3-O-（3,6-脱水-β-d-吡喃半乳糖苷）-α-d-吡喃半乳糖苷（3）和甲基3,6-脱水-4-O-βd-吡喃半乳糖苷-α-d-吡喃半乳糖苷（4）已经使用三种偶联方法合成了立体选择性。使用乙酰化衍生物作为给体，三氟甲磺酸三甲基甲硅烷基酯作为催化剂，可以达到可接受的收率。在甲醇甲醇钠中进行分子内甲苯磺酸酯置换以形成3,6-脱水环。
• Synthesis and conformational studies of carrabiose and its 4′-sulphate and 2,4′-disulphate
  作者：Enrique Parra、Hugo-Norberto Caro、Jesús Jiménez-Barbero、Manuel Martín-Lomas、Manuel Bernabé

  DOI：10.1016/0008-6215(90)80087-j

  日期：1990.12

  Methyl alpha-carrabioside (13), and its 4-sulphate (19) and 2,4-disulphate (20) have been synthesised via glycosylation of methyl 3,6-anhydro-2-O-benzyl-alpha-D-galactopyranoside with 2,3,6-tri-O-acetyl-4-O-benzyl-beta-D-galactopyranosyl bromide and subsequent partial or complete debenzylation, sulphation, and deprotection of the resulting disaccharide derivatives. Conformational studies have been carried out on 13, 19, and 20 on the basis of 1D and 2D 1H-n.m.r. spectroscopy and molecular mechanics calculations.