phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside | 502181-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylselanyl-4-prop-2-enoxyoxane
• CAS: 502181-38-6
• 化学式: C₃₆H₃₈O₅Se
• 分子量: 629.655
• InChiKey: JVIQOUATOUEQLU-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

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 、 silver trifluoromethanesulfonate 、 三氟甲烷磺酸甲酯 、 环己基溴化镁 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 41.08h， 生成 methyl 3,4,6-tri-O-benzyl-α-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：

  1,2,4,6-四-O-乙酰基-3-O-烯丙基-β-D-吡喃葡萄糖 在 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.75h， 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

• Total synthesis of the Glc3Man N-glycan tetrasaccharide
  作者：S.C Ennis、I Cumpstey、A.J Fairbanks、T.D Butters、M Mackeen、M.R Wormald

  DOI：10.1016/s0040-4020(02)01221-8

  日期：2002.11

  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.