phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside | 502181-48-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside
• CAS: 502181-48-8
• 化学式: C₂₁H₂₆O₈Se
• 分子量: 485.393
• InChiKey: OJJBDJABGSWCDM-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 在 吡啶 、 titanium(IV) isopropylate 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 三氟甲烷磺酸甲酯 、 环己基溴化镁 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.83h， 生成 methyl (2-O-allyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Total synthesis of the Glc3Man N-glycan tetrasaccharide

  摘要：

  The total synthesis of the tetrasaccharide Glcalpha(1-->2)Glcalpha(1-->3)Glcalpha(1-->3)ManalphaOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)01221-8
• 作为产物：
  描述：

  3-O-allyl-D-glucopyranose 在 三氟化硼乙醚 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of the Glc3Man N-glycan tetrasaccharide

  摘要：

  The total synthesis of the tetrasaccharide Glcalpha(1-->2)Glcalpha(1-->3)Glcalpha(1-->3)ManalphaOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)01221-8

文献信息

• Elimination reactions of glycosyl selenoxides
  作者：David J. Chambers、Graham R. Evans、Antony J. Fairbanks

  DOI：10.1016/j.tet.2004.07.005

  日期：2004.9

  Glycosyl selenoxides, generated in situ from selenoglycosides by a Sharpless-type oxidation, undergo facile syn elimination leading to 2-hydroxy and 2-amino glycals in high yield.

  糖苷亚硒酸酯是通过Sharpless型氧化从硒代糖苷原位生成的，可以轻松地进行syn消除，从而以高收率得到2-羟基和2-氨基糖基。