(6S)-<6-2H>Methyl-β-D-galactopyranoside | 35669-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6S)-<6-2H>Methyl-β-D-galactopyranoside
• 英文别名: methyl (6S)-(6-(2)H1)-β-D-galactopyranoside；methyl 6(S)-β-D-(6-2H)galactopyranoside；methyl 6-(S)-2H1-β-D-galactopyranoside；Methyl-β-D-galactopyranosid-6-d；(2R,3R,4S,5R,6R)-2-[(S)-deuterio(hydroxy)methyl]-6-methoxyoxane-3,4,5-triol
• CAS: 35669-28-4
• 化学式: C₇H₁₄O₆
• 分子量: 195.177
• InChiKey: HOVAGTYPODGVJG-BMWBFFNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6S)-<6-2H>Methyl-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl 6-(S)-2H-2,3,4-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Preferred conformation about the C5-C6 bond of N-acetylneuraminyl(2-6)-D-galacto- and -D-glucopyranosides in solution

  摘要：

  Diastereoselective deuteration and H-1 NMR spectroscopy were applied in a conformational study of the C5-C6 bond in four stereoisomeric methyl N-acetylneuraminyl(2-6)-beta-D-hexopyranosides [NeuNAc-alpha(2-6)Gal, NeuNAc-beta-(2-6)Gal, NeuNAc-alpha-(2-6)Glc, and NeuNAc-beta-(2-6)Glc]. In aqueous solution, NeuNAc-alpha-(2-6)Gal prefers a gt conformer (gg:gt:tg = ca. 20:60:20), NeuNAc(2-6)Glc isomers prefer a gg (gg:gt:tg = ca. 60:40:0), and NeuNAc-beta-(2-6)Gal exists equally in the three conformers.

  DOI：

  10.1021/jo00005a015
• 作为产物：
  描述：

  methyl (6S)-(6-(2)H1)-tetra-O-acetyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以70 mg的产率得到(6S)-<6-2H>Methyl-β-D-galactopyranoside
  参考文献：
  名称：

  Bock, Klaus; Refn, Susanne, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, p. 469 - 472

  摘要：

  DOI：

文献信息

• Conformational analysis of sialyloligosaccharides
  作者：Subramaniam Sabesan、Klaus Bock、James C. Paulson

  DOI：10.1016/0008-6215(91)84084-r

  日期：1991.9

  through 1H-1H coupling constants. Of all the (2----6) sialosides examined, only the deuterated di- and tri-saccharide afforded useful nuclear Overhauser enhancement data that could be used to evaluate the global minimum-energy conformations. Hard-sphere exoanomeric effect calculations estimated the glycosidic torsion angles for the global minimum-energy conformer of alpha-D-NeuAc-(2----6)-beta-D-Gal linkages

  基于选定唾液酸苷的核磁共振数据，已经分析了糖蛋白的N-和O-连接的碳水化合物基团中作为末端序列存在的几种唾液寡糖的构象特性。检查的化合物包括α-D-NeuAc-（2 ---- 6）-β-D-Gal-（1 ---- 4）-β-D-GlcNAc，α-D-NeuAc-（ 2 ---- 3）-beta-D-Gal-（1 ---- 4）-beta-D-GlcNAc，alpha-D-NeuAc-（2 ---- 3）-beta-D-Gal- （1 ---- 3）-beta-D-GlcNAc和alpha-D-NeuAc-（2 ---- 3）-beta-D-Gal-（1 ---- 3）-beta-D- GalNAc系列。通过6-甲基-β-D-吡喃半乳糖苷和乳糖苷的6-氘代半乳糖衍生物的酶促唾液酸化，制备了两种氘代唾液酸苷。这些对于通过1H-1H偶合常数明确建立半乳糖的柔性C-6亚甲基单元的“ gt”取向是有
• The preferred rotamer about the C₅—C₆ bond of <scp>D</scp>-galactopyranoses and the stereochemistry of dehydrogenation by <scp>D</scp>-galactose oxidase
  作者：Hiroshi Ohrui、Yoshihiro Nishida、Hiroko Higuchi、Hiroshi Hori、Hiroshi Meguro

  DOI：10.1139/v87-191

  日期：1987.6.1

  ¹H nuclear magnetic resonance studies on D-galactopyranoses with chirally deuterated hydroxymethyl groups revealed that the preferred rotamer about the C₅—C₆ bond of the D-galactopyranoses was not tg but gt. Studies on the stereochemistry of dehydrogenation of D-galactose oxidase from Dactyliumdendroides with chirally pure deuterated methyl β-D-galactopyranosides showed that there were two mechanisms for the enzymatic reaction: an efficient pro-S hydrogen atom specific oxidation and a far less efficient non-specific or pro-R specific oxidation.

  使用手性氘代羟甲基基团的核磁共振技术研究D-半乳糖苷的结构，发现其C5-C6键的优先构象不是tg而是gt。使用手性纯的氘代甲基β-D-半乳糖苷研究Dactyliumdendroides的D-半乳糖氧化酶的立体化学，发现酶反应存在两种机制：高效的pro-S氢原子特异性氧化和远不如前者的非特异性或pro-R特异性氧化。
• Preferred conformation about the C5-C6 bond of N-acetylneuraminyl(2-6)-D-galacto- and -D-glucopyranosides in solution
  作者：Hiroshi Ohrui、Yoshihiro Nishida、Hisashi Itoh、Hiroshi Meguro

  DOI：10.1021/jo00005a015

  日期：1991.3

  Diastereoselective deuteration and H-1 NMR spectroscopy were applied in a conformational study of the C5-C6 bond in four stereoisomeric methyl N-acetylneuraminyl(2-6)-beta-D-hexopyranosides [NeuNAc-alpha(2-6)Gal, NeuNAc-beta-(2-6)Gal, NeuNAc-alpha-(2-6)Glc, and NeuNAc-beta-(2-6)Glc]. In aqueous solution, NeuNAc-alpha-(2-6)Gal prefers a gt conformer (gg:gt:tg = ca. 20:60:20), NeuNAc(2-6)Glc isomers prefer a gg (gg:gt:tg = ca. 60:40:0), and NeuNAc-beta-(2-6)Gal exists equally in the three conformers.
• Bock, Klaus; Refn, Susanne, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, p. 469 - 472
  作者：Bock, Klaus、Refn, Susanne

  DOI：——

  日期：——