2,4,6-tri-O-benzyl-3-O-tert-butyldiphenylsilyl-α-D-mannoside | 464189-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tri-O-benzyl-3-O-tert-butyldiphenylsilyl-α-D-mannoside
• 英文别名: Bn(-2)[TBDPS(-3)][Bn(-4)][Bn(-6)]Man(a)-SPh；[(2R,3R,4S,5S,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-4-yl]oxy-tert-butyl-diphenylsilane
• CAS: 464189-93-3
• 化学式: C₄₉H₅₂O₅SSi
• 分子量: 781.1
• InChiKey: YSGQZEZSXQZIGD-ZEWOKLPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.84
• 重原子数：
  56
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-benzyl-3-O-tert-butyldiphenylsilyl-α-D-mannoside 在 吡啶 、 氢氟酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、999.99 MPa 条件下， 反应 15.0h， 以85%的产率得到phenyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Desilylation under high pressure

  摘要：

  Cleavage of tert-butyldiphenylsilyl (TBDPS) ether was examined under high pressure conditions (1.0 GPa) using HF pyridine in DMF. This method proved to be exceptionally suitable for deprotecting the TBDPS group that resides at the sterically hindered position. Under these conditions, various types of other hydroxyl protecting groups (i.e. benzyl, p-methoxybenzyl, trityl, isopropylidene, cyclohexylidene, allyl, phthaloyl) as well as O- and S-glycosidic linkages were preserved. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00538-5
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 咪唑 、 甲醇 、 sodium hydroxide 、 {Ir(COD)[PCH₃(C₆H₅)2]}PF₆ 、 camphor-10-sulfonic acid 、 氢气 、 四丁基硫酸氢铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 54.0h， 生成 2,4,6-tri-O-benzyl-3-O-tert-butyldiphenylsilyl-α-D-mannoside
  参考文献：
  名称：

  Synthesis of Monoglucosylated High-Mannose-Type Dodecasaccharide, a Putative Ligand for Molecular Chaperone, Calnexin, and Calreticurin

  摘要：

  Convergent and stereoselective synthetic routes to Man9GlcNAc2 (1b), alpha-Glc1M9GlcNAc2 (2b), and its stereoisomer beta-Glc1M9GlcNAc2 (3) were established. Interaction analysis of 2b with CRT was measured by 1H NMR spectroscopy, and the first NMR-based evidence for the specific binding of CRT to 2b was obtained.

  DOI：

  10.1021/ja021288q

文献信息

• Synthesis of Monoglucosylated High-Mannose-Type Dodecasaccharide, a Putative Ligand for Molecular Chaperone, Calnexin, and Calreticurin
  作者：Ichiro Matsuo、Megumi Wada、Shino Manabe、Yoshiki Yamaguchi、Keisuke Otake、Koichi Kato、Yukishige Ito

  DOI：10.1021/ja021288q

  日期：2003.3.1

  Convergent and stereoselective synthetic routes to Man9GlcNAc2 (1b), alpha-Glc1M9GlcNAc2 (2b), and its stereoisomer beta-Glc1M9GlcNAc2 (3) were established. Interaction analysis of 2b with CRT was measured by 1H NMR spectroscopy, and the first NMR-based evidence for the specific binding of CRT to 2b was obtained.
• Desilylation under high pressure
  作者：Ichiro Matsuo、Megumi Wada、Yukishige Ito

  DOI：10.1016/s0040-4039(02)00538-5

  日期：2002.4

  Cleavage of tert-butyldiphenylsilyl (TBDPS) ether was examined under high pressure conditions (1.0 GPa) using HF pyridine in DMF. This method proved to be exceptionally suitable for deprotecting the TBDPS group that resides at the sterically hindered position. Under these conditions, various types of other hydroxyl protecting groups (i.e. benzyl, p-methoxybenzyl, trityl, isopropylidene, cyclohexylidene, allyl, phthaloyl) as well as O- and S-glycosidic linkages were preserved. (C) 2002 Elsevier Science Ltd. All rights reserved.