6-O-(β-D-glucopyranosyl)-D-galactopyranose | 4604-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(β-D-glucopyranosyl)-D-galactopyranose
• 英文别名: 6-O-(β-D-glucopyranosyl)-D-galactose；6-O-β-D-Galactopyranosyl-D-galactose；6-O-(B-D-Galactopyranosyl)-D-galactopyranose；(3R,4S,5R,6R)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 4604-26-6
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: DLRVVLDZNNYCBX-XIEPDHIPSA-N

物化性质

• 熔点：
  126-128 °C
• 沸点：
  662.8±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  氨甲酸,(2-氟环丙基)-,1,1-二甲基乙基酯,顺-(9CI) 在 palladium on activated charcoal lithium hydroxide 、 四甲基硫脲 、 W-2 Raney nickel 、 氢气 、 甲基三辛基氯化铵 、 对甲苯磺酸 、 2,4-双(4-苯氧苯基)-1,3-二硫杂-2,4-二磷杂环丁烷-2,4-二硫化物 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 256.0h， 生成 6-O-(β-D-glucopyranosyl)-D-galactopyranose
  参考文献：
  名称：

  Redox glycosidation: stereoselective syntheses of (1.fwdarw.6) linked disaccharides via thionoester intermediates

  摘要：

  Perbenzyl derivatives of the disaccharides benzyl 6-O-(alpha(and beta)-D-glucopyranosyl)-alpha-D-galactopyranoside and benzyl 6-O-(alpha(and beta)-D-mannopyranosyl)-alpha-D-galactopyranoside were each prepared in a stereoselective manner by acylation, thionation, and reductive desulfurization. The use of 2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (4b) as a mild thionation reagent for esters and lactones is also described.

  DOI：

  10.1021/jo00036a012

文献信息

• A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit
  作者：Cecile du Mortier、Oscar Varela、Rosa M. de Lederkremer

  DOI：10.1016/0008-6215(89)84087-x

  日期：1989.6

  The lactonic disaccharide 2,3,5-tri- O -benzoyl-6- O -(2,3,4,6-tetra- O -acetyl-β- d -glucopyranosyl)- d -galactono-1,4-lactone ( 7 ) was prepared by condensing 6- O -trityl-2,3,5-tri- O -benzoyl- d -galactono-1,4-lactone ( 2 ) with 2,3,4,6-tetra- O -acetyl-α- d -glucopyranosyl bromide ( 4 ) or with 1,2,3,4,6-penta- O -acetyl-β- d -glucopyranose ( 6 ). The reaction was carried out using various catalysts

  摘要内酯二糖2,3,5-三-O-苯甲酰基-6-O-（2,3,4,6-四-O-乙酰基-β-d-吡喃葡萄糖基）-d-半乳糖-1,4-内酯（7）是通过将6-O-三苯甲基-2,3,5-三-O-苯甲酰基-d-半乳糖-1,4-内酯（2）与2,3,4,6-四-O缩合而制得-乙酰基-α-d-吡喃葡萄糖基溴化物（4）或与1,2,3,4,6-戊-O-乙酰基-β-d-吡喃葡萄糖（6）。使用各种催化剂进行反应。在三氟甲磺酸银或氯化锡（IV）的存在下，立体选择性地形成1,2-反式糖苷键，以高收率得到化合物7。然而，由汞盐催化的2,3,5-三-O-苯甲酰基-d-半内酯-1,4-内酯（3）与4的缩合得到3,4,6-三-O-乙酰基-1,2 -O-[1（S）-（2,3,5-三-O-苯甲酰基-d-半乳糖基-1，以4-内酯-6-烷氧基）亚乙基]-α-d-吡喃葡萄糖（5）为主要产物。用双（3-甲基-2-丁基）硼烷还原7的内酯功能导致2
• Redox glycosidation: stereoselective syntheses of (1.fwdarw.6) linked disaccharides via thionoester intermediates
  作者：Anthony G. M. Barrett、Albert C. Lee

  DOI：10.1021/jo00036a012

  日期：1992.5

  Perbenzyl derivatives of the disaccharides benzyl 6-O-(alpha(and beta)-D-glucopyranosyl)-alpha-D-galactopyranoside and benzyl 6-O-(alpha(and beta)-D-mannopyranosyl)-alpha-D-galactopyranoside were each prepared in a stereoselective manner by acylation, thionation, and reductive desulfurization. The use of 2,4-bis(4-phenoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (4b) as a mild thionation reagent for esters and lactones is also described.