allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside | 647027-51-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside
• 英文别名: [(2S,3R,4S,5R,6S)-2-[(2R,3S,4R,5R,6R)-5-azido-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylmethoxy-6-prop-2-enoxyoxan-3-yl]oxy-5-(9H-fluoren-9-ylmethoxycarbonyloxy)-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] 4-oxopentanoate
• CAS: 647027-51-8
• 化学式: C₇₂H₇₇N₃O₁₄Si
• 分子量: 1236.5
• InChiKey: UOSHRLQOFPZBIZ-DOISRCGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.28
• 重原子数：
  90
• 可旋转键数：
  32
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside 在 sodium acetate 、 溶剂黄146 、 palladium dichloride 作用下， 生成 4-Oxo-pentanoic acid (2S,3R,4S,5R,6S)-2-[(2R,3S,4R,5R)-5-azido-4-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-tetrahydro-pyran-3-yloxy]-4-benzyloxy-6-benzyloxymethyl-5-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  New Set of Orthogonal Protecting Groups for the Modular Synthesis of Heparan Sulfate Fragments

  摘要：

  [GRAPHICS]Six strategically chosen monosaccharide building blocks, which are protected by a novel set of four orthogonal protecting groups (Lev, Fmoc, TBDPS, and All), can be employed for the efficient synthesis of the 20 disaccharide moieties found in heparan sulfate. The properly protected disaccharide building blocks can be converted into glycosyl donors and acceptors, which can be used for the modular synthesis of a wide range of well-defined oligosaccharides that differ in sulfation pattern.

  DOI：

  10.1021/ol0359261
• 作为产物：
  描述：

  3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α,β-L-idopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside
  参考文献：
  名称：

  New Set of Orthogonal Protecting Groups for the Modular Synthesis of Heparan Sulfate Fragments

  摘要：

  [GRAPHICS]Six strategically chosen monosaccharide building blocks, which are protected by a novel set of four orthogonal protecting groups (Lev, Fmoc, TBDPS, and All), can be employed for the efficient synthesis of the 20 disaccharide moieties found in heparan sulfate. The properly protected disaccharide building blocks can be converted into glycosyl donors and acceptors, which can be used for the modular synthesis of a wide range of well-defined oligosaccharides that differ in sulfation pattern.

  DOI：

  10.1021/ol0359261

文献信息

• New Set of Orthogonal Protecting Groups for the Modular Synthesis of Heparan Sulfate Fragments
  作者：Arati Prabhu、Andre Venot、Geert-Jan Boons

  DOI：10.1021/ol0359261

  日期：2003.12.1

  [GRAPHICS]Six strategically chosen monosaccharide building blocks, which are protected by a novel set of four orthogonal protecting groups (Lev, Fmoc, TBDPS, and All), can be employed for the efficient synthesis of the 20 disaccharide moieties found in heparan sulfate. The properly protected disaccharide building blocks can be converted into glycosyl donors and acceptors, which can be used for the modular synthesis of a wide range of well-defined oligosaccharides that differ in sulfation pattern.