2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl chloride | 85993-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl chloride
• 英文别名: [(3S,4S,5R,6R)-2-chloro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 85993-78-8
• 化学式: C₂₉H₃₁ClO₆
• 分子量: 511.015
• InChiKey: BDYLUCCCTCPTKM-MJOWNYDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranosyl chloride 在 正丁基锂 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  通过分子内苷元递送 (IAD) 对 2-O-烯丙基保护的糖基供体进行立体选择性顺式糖基化

  摘要：

  2-O-烯丙基保护的糖基供体可以通过涉及双键异构化、N-碘代琥珀酰亚胺介导的与糖基受体的束缚和随后的分子内糖基化（分子内苷元递送，IAD）的三步序列进行立体选择性糖基化。

  DOI：

  10.1039/b004522p

文献信息

• Shao; Guo, Polish Journal of Chemistry, 2005, vol. 79, # 2, p. 297 - 307
  作者：Shao、Guo

  DOI：——

  日期：——
• Solid-phase synthesis of CD52 glycopeptide and an efficient route to Asn-core pentasaccharide conjugate
  作者：Zhong-Wu Guo、Yuko Nakahara、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0968-0896(97)00126-0

  日期：1997.10

  The intact peptide sequence (18) as well as its glycoform carrying an N-linked core pentasaccharide (I) of CD52 antigen were prepared by means of solid-phase synthesis employing Fmoc-amino acids and benzyl-protected oligo saccharide-asparagine conjugate (3) as building blocks. It was concluded that the pentasaccharide structure had little influence on further peptide elongation in solid-phase synthesis and the benzylated pentasaccharide moiety was sufficiently stable to the 95% TFA acidic conditions used to release glycopeptide from the supporting resin. The paper also describes an efficient route leading to asparagine-core pentasaccharide conjugate (3) which was prepared in seven steps for an overall yield of 23% from monosaccharide units 5, 6, 7 and 8. (C) 1997 Elsevier Science Ltd.
• A practical and efficient synthesis of complex-type biantennary heptasaccharide-asparagine conjugate, a key building block for the synthesis of complex N-linked glycopeptides
  作者：Zhong-Wu Guo、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0040-4039(97)01036-8

  日期：1997.7

  The complex-type biantennary heptasaccharide-asparagine conjugate(2) of N-linked glycoproteins was synthesized from monosaccharide units 3, 4, 6, 7 and 8 in 7 steps with an overall yield of 18.4%. (C) 1997 Elsevier Science Ltd.
• Synthetic study on a novel Asn-linked core structure: synthesis of a pentasaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-β-d-Man-(1→4)-[β-d-GlcNAc-(1→6)]-β-d-GlcNAc→OMp11Mp=p-meth
  作者：Zhong-Wu Guo、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0008-6215(98)00031-7

  日期：1998.1

  Synthesis of a pentasaccharide alpha-DMan-(1-->3)-[alpha-D-Man-(1-->6)]-beta-D-Man-(1-->4)-[beta-D-GlcNAc(1-->6)]-beta-D-GlcNAc-->OMp (2) is described. A comparison between the H-1 NMR data of 2 and those of a novel Asn-linked core structure 1 containing a new GlcNAc residue suggests an alpha-D-configuration for the new linkage. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of a hexasaccharide that forms part of an alveolar glycoprotein
  作者：Herbert Baumann、Hans Lönn、Jörgen Lönngren

  DOI：10.1016/0008-6215(83)88200-7

  日期：1983.4