Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside | 138459-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside
• 英文别名: [(3aR,4R,6S,7S,7aS)-7-bromo-6-[(2S,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methanol
• CAS: 138459-06-0
• 化学式: C₃₇H₄₅BrO₉
• 分子量: 713.663
• InChiKey: QQNIAXVGRPGFBC-AOTPQFQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以57%的产率得到Methyl 4-deoxy-4-C-(1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside
  参考文献：
  名称：

  Synthesis of .alpha.-methyl 1',2'-dideoxycellobioside: a novel C-disaccharide

  摘要：

  Bromonium ion induced 6-endo-trig cyclizations of E olefine derived from D-arabinose provide a stereoselective route to 2'-deoxyglucono-beta-C-glycosides. Use of delta-alkenols containing allylic isopropylidenes (i.e., 1) prevents formation of furan products due to the highly strained transition state necessary for formation of the trans [3.3.0] bicyclic systems. Because the exo-anomeric carbon is not involved in the cyclization, previously established stereocenters at this carbon are left intact. Application of this methodology to the synthesis of alpha-methyl 1',2'-dideoxycellobioside (22) is presented. The restricted rotation about the bond connecting the two sugars affords a unique staggared conformation of the disaccharide.

  DOI：

  10.1021/jo00029a024
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-D-arabinose diethyldithioacetal 在 咪唑 、 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 四丁基氟化铵 、 溴 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 65.42h， 生成 Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside
  参考文献：
  名称：

  Synthesis of .alpha.-methyl 1',2'-dideoxycellobioside: a novel C-disaccharide

  摘要：

  Bromonium ion induced 6-endo-trig cyclizations of E olefine derived from D-arabinose provide a stereoselective route to 2'-deoxyglucono-beta-C-glycosides. Use of delta-alkenols containing allylic isopropylidenes (i.e., 1) prevents formation of furan products due to the highly strained transition state necessary for formation of the trans [3.3.0] bicyclic systems. Because the exo-anomeric carbon is not involved in the cyclization, previously established stereocenters at this carbon are left intact. Application of this methodology to the synthesis of alpha-methyl 1',2'-dideoxycellobioside (22) is presented. The restricted rotation about the bond connecting the two sugars affords a unique staggared conformation of the disaccharide.

  DOI：

  10.1021/jo00029a024

文献信息

• Synthesis of .alpha.-methyl 1',2'-dideoxycellobioside: a novel C-disaccharide
  作者：Robert W. Armstrong、Bradley R. Teegarden

  DOI：10.1021/jo00029a024

  日期：1992.1

  Bromonium ion induced 6-endo-trig cyclizations of E olefine derived from D-arabinose provide a stereoselective route to 2'-deoxyglucono-beta-C-glycosides. Use of delta-alkenols containing allylic isopropylidenes (i.e., 1) prevents formation of furan products due to the highly strained transition state necessary for formation of the trans [3.3.0] bicyclic systems. Because the exo-anomeric carbon is not involved in the cyclization, previously established stereocenters at this carbon are left intact. Application of this methodology to the synthesis of alpha-methyl 1',2'-dideoxycellobioside (22) is presented. The restricted rotation about the bond connecting the two sugars affords a unique staggared conformation of the disaccharide.