methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 136824-12-9

• 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->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside；Bn(-3)[Bn(-4)][Bn(-6)]Man(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1Me；(2S,3S,4R,5R,6R)-2-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 136824-12-9
• 化学式: C₅₅H₆₀O₁₁
• 分子量: 897.075
• InChiKey: RKVLLPBYSUJMLO-HZOOEWRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以95%的产率得到β-D-Manp-(1->4)-α-D-Glcp-OMe
  参考文献：
  名称：

  Barresi, Frank; Hindsgaul, Ole, Journal of the American Chemical Society, 1991, vol. 113, # 24, p. 9376 - 9377

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 在 N-碘代丁二酰亚胺 、 2,6-二叔丁基-4-甲基吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.17h， 生成 methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Barresi, Frank; Hindsgaul, Ole, Canadian Journal of Chemistry, 1994, vol. 72, # 6, p. 1447 - 1465

  摘要：

  DOI：

文献信息

• Stereospecific Synthesis of 1,2-<i>cis</i> Glycosides by Vinyl-Mediated IAD
  作者：Kampanart Chayajarus、David J. Chambers、Majid J. Chughtai、Antony J. Fairbanks

  DOI：10.1021/ol048427o

  日期：2004.10.1

  (GRAPHICS)Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD). The use of such an intramolecular glycosylation strategy furnishes the desired alpha-gluco and beta-manno disaccharides in an entirely stereoselective manner.
• 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
• Practical Synthesis of .beta.-D-Xyl-(1.fwdarw.2)-.beta.-D-Man-(1.fwdarw.4)-.alpha.-D-Glc-OMe, a Trisaccharide Component of the Hyriopsis schlegelii Glycosphingolipid
  作者：Frieder W. Lichtenthaler、Thomas Schneider-Adams、Stefan Immel

  DOI：10.1021/jo00101a036

  日期：1994.11

  By employing the readily accessible (preceding paper in this issue) 3,4,6-tri-O-benzyl-alpha-D-arabino-hexosyl bromide (1) as an indirect, beta-specific mannosyl donor, a practical three-step synthesis was elaborated for methyl xylosyl-beta(1-->2)-mannosyl-beta(1-->4)-glucoside (11), a trisaccharide component of Hyriopsis schlegelii ceramide oligosaccharides. Key steps were the silver aluminosilicate-induced, beta-specific glycosidation of 1 with methyl 2,3,6-tri-O-benzyl-alpha-D-glucoside and the silver triflate-promoted beta-xylosylation with 2,3,4-tri-O-benzoyl-alpha-D-xylosyl bromide. The overall yield amounted to a satisfactory 47%.
• Barresi, Frank; Hindsgaul, Ole, Canadian Journal of Chemistry, 1994, vol. 72, # 6, p. 1447 - 1465
  作者：Barresi, Frank、Hindsgaul, Ole

  DOI：——

  日期：——
• Barresi, Frank; Hindsgaul, Ole, Journal of the American Chemical Society, 1991, vol. 113, # 24, p. 9376 - 9377
  作者：Barresi, Frank、Hindsgaul, Ole

  DOI：——

  日期：——