methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside | 173910-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]Man(b1-6)[Bn(-2)][Bn(-3)]a-Glc1Me；(2R,3S,4R,5R,6R)-2-[[(2R,3R,4S,5R,6S)-3-hydroxy-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 173910-83-3
• 化学式: C₄₈H₅₄O₁₁
• 分子量: 806.95
• InChiKey: FRNUOWNKOSUZAC-MBVIYEPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of β-Mannopyranosides via the Temporary Silicon Connection Method

  摘要：

  DOI：

  10.1021/ja9532291
• 作为产物：
  描述：

  2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride 在 2,6-二叔丁基-4-甲基吡啶 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 tin(ll) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 94.0h， 生成 methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Allyl protecting group mediated intramolecular aglycon delivery: optimisation of mixed acetal formation and mechanistic investigation

  摘要：

  An efficient protocol for the formation of alpha-iodo mixed acetals, the first step of allyl-mediated 1AD, by reaction of allyl-derived enol ethers and alcohols, using I-2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, is reported. This reagent combination is capable of tethering glycosyl donors to the secondary alcohol groups of a variety of glycosyl acceptors including mono-, di- and trisaccharides. Mechanistic studies confirm the intramolecular nature of the glycosylation reaction, whilst the attempted use of diol glycosyl acceptors reveals limitations of both regio- and stereo selectivity in the glycosylation step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.003

文献信息

• Allyl protecting group mediated intramolecular aglycon delivery: optimisation of mixed acetal formation and mechanistic investigation
  作者：Ian Cumpstey、Kampanart Chayajarus、Antony J. Fairbanks、Alison J. Redgrave、Christopher M.P. Seward

  DOI：10.1016/j.tetasy.2004.09.003

  日期：2004.10

  An efficient protocol for the formation of alpha-iodo mixed acetals, the first step of allyl-mediated 1AD, by reaction of allyl-derived enol ethers and alcohols, using I-2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, is reported. This reagent combination is capable of tethering glycosyl donors to the secondary alcohol groups of a variety of glycosyl acceptors including mono-, di- and trisaccharides. Mechanistic studies confirm the intramolecular nature of the glycosylation reaction, whilst the attempted use of diol glycosyl acceptors reveals limitations of both regio- and stereo selectivity in the glycosylation step. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereoselective Synthesis of β-Mannopyranosides via the Temporary Silicon Connection Method
  作者：Gilbert Stork、James J. La Clair

  DOI：10.1021/ja9532291

  日期：1996.1.1