methyl 6,3'-O-[3-(diisopropylsilyl)benzyl]-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside | 522632-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6,3'-O-[3-(diisopropylsilyl)benzyl]-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside
• 英文别名: (1R,3R,4S,5R,6S,8R,19S,20R,22R,25R,27R)-6-methoxy-22-phenyl-4,5,27-tris(phenylmethoxy)-11,11-di(propan-2-yl)-2,7,10,18,21,23,26-heptaoxa-11-silapentacyclo[17.7.1.112,16.03,8.020,25]octacosa-12,14,16(28)-triene
• CAS: 522632-99-1
• 化学式: C₅₄H₆₄O₁₁Si
• 分子量: 917.181
• InChiKey: JHNZKFAMPJNIDV-PAMRUSPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.93
• 重原子数：
  66
• 可旋转键数：
  13
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 6,3'-O-[3-(diisopropylsilyl)benzyl]-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以91%的产率得到methyl O-{2-O-benzyl-4,6-O-benzylidene-3-O-[3-(hydroxyisopropylsilyl)benzyl]-α-D-glucopyranosyl}-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Reiterative Intramolecular Glycosylation Supported by a Rigid Spacer

  摘要：

  This paper describes a synthesis of trisaccharide 1 by reiterative intramolecular glycosidation with 5-(bromomethyl)-2-methylbenzoic acid (5a) as starting material for the generation of a rigid spacer. Intramolecular glycosidation of donor-acceptor-tethered compound 24 yielded disaccharide 25. Transesterification of 25 afforded 26, which generated a new linking centre for the next spacer. Repetition of the previous cycle on 26 yielded trisaccharide 1, which again presents an extension point for the synthesis of higher saccharides. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2003).

  DOI：

  10.1002/1099-0690(200301)2003:1<128::aid-ejoc128>3.0.co;2-s
• 作为产物：
  描述：

  ethyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 叔丁基锂 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.5h， 生成 methyl 6,3'-O-[3-(diisopropylsilyl)benzyl]-(2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1 - 4)-2,3-di-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Reiterative Intramolecular Glycosylation Supported by a Rigid Spacer

  摘要：

  This paper describes a synthesis of trisaccharide 1 by reiterative intramolecular glycosidation with 5-(bromomethyl)-2-methylbenzoic acid (5a) as starting material for the generation of a rigid spacer. Intramolecular glycosidation of donor-acceptor-tethered compound 24 yielded disaccharide 25. Transesterification of 25 afforded 26, which generated a new linking centre for the next spacer. Repetition of the previous cycle on 26 yielded trisaccharide 1, which again presents an extension point for the synthesis of higher saccharides. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2003).

  DOI：

  10.1002/1099-0690(200301)2003:1<128::aid-ejoc128>3.0.co;2-s

文献信息

• Reiterative Intramolecular Glycosylation Supported by a Rigid Spacer
  作者：Soumendu Paul、Matthias Müller、Richard R. Schmidt

  DOI：10.1002/1099-0690(200301)2003:1<128::aid-ejoc128>3.0.co;2-s

  日期：2003.1

  This paper describes a synthesis of trisaccharide 1 by reiterative intramolecular glycosidation with 5-(bromomethyl)-2-methylbenzoic acid (5a) as starting material for the generation of a rigid spacer. Intramolecular glycosidation of donor-acceptor-tethered compound 24 yielded disaccharide 25. Transesterification of 25 afforded 26, which generated a new linking centre for the next spacer. Repetition of the previous cycle on 26 yielded trisaccharide 1, which again presents an extension point for the synthesis of higher saccharides. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2003).