1-O-(Boc-L-Ser)-2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranoside | 1008130-96-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-(Boc-L-Ser)-2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranoside
• 英文别名: methyl N-(tert-butoxycarbonyl)-O-(2,3:4,6-di-O-isopropylidene-α-D-mannopyranose)-L-serine；methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[[(1R,2S,6S,7S,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl]oxy]propanoate
• CAS: 1008130-96-8
• 化学式: C₂₁H₃₅NO₁₀
• 分子量: 461.51
• InChiKey: IOOQYTFKHFJODJ-XFQLPGMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [(1R,2S,6S,7R,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl] 2,2,2-trichloroethanimidate 、 Boc-L-丝氨酸甲酯 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到1-O-(Boc-L-Ser)-2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranoside
  参考文献：
  名称：

  Cationic Palladium(II)-Catalyzed Stereoselective Glycosylation with Glycosyl Trichloroacetimidates

  摘要：

  [GRAPHICS]The development of a new method for stereoselective glycosylation with glycosyl trichloroacetimidate donors employing cationic palladium(II), Pd(CH3CN)(4)(BF4)(2), is described. This process employs Pd(CH3CN)(4)(BF4)(2) as an efficient activator, providing access to a variety of disaccharides and glycopeptides. This reaction is highly stereoselective and proceeds under mild conditions with low catalyst loading. Interestingly, this palladium catalysis directs beta-glucosylations in the absence of classical neighboring group participation.

  DOI：

  10.1021/jo702436p

文献信息

• Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea
  作者：Qiuhan Li、Samuel M. Levi、Eric N. Jacobsen

  DOI：10.1021/jacs.0c04255

  日期：2020.7.8

  We report highly beta-selective bis-thioureas-catalyzed 1,2-cis-O-pyranosylations employing easily accessible acetonide-protected donors. A wide variety of alcohol nucleophiles, including complex natural products, glycosides, and amino acids were beta-mannosylated and beta-rhamnosylated successfully using an operationally simple protocol under mild and neutral conditions. Less nucleophilic acceptors such as phenols were also glycosylated efficiently in excellent yields and with high beta-selectivities.
• Cationic Palladium(II)-Catalyzed Stereoselective Glycosylation with Glycosyl Trichloroacetimidates
  作者：Jaemoon Yang、Colleen Cooper-Vanosdell、Enoch A. Mensah、Hien M. Nguyen

  DOI：10.1021/jo702436p

  日期：2008.2.1

  [GRAPHICS]The development of a new method for stereoselective glycosylation with glycosyl trichloroacetimidate donors employing cationic palladium(II), Pd(CH3CN)(4)(BF4)(2), is described. This process employs Pd(CH3CN)(4)(BF4)(2) as an efficient activator, providing access to a variety of disaccharides and glycopeptides. This reaction is highly stereoselective and proceeds under mild conditions with low catalyst loading. Interestingly, this palladium catalysis directs beta-glucosylations in the absence of classical neighboring group participation.