[(2S,3R,4R,5S)-4,5-diacetyloxy-6-bis(phenylmethoxy)phosphanyloxy-2-methyloxan-3-yl] acetate | 149717-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4R,5S)-4,5-diacetyloxy-6-bis(phenylmethoxy)phosphanyloxy-2-methyloxan-3-yl] acetate
• CAS: 149717-37-3
• 化学式: C₂₆H₃₁O₁₀P
• 分子量: 534.5
• InChiKey: GRTCBRAUUPJYDV-QUNCFXGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5S)-4,5-diacetyloxy-6-bis(phenylmethoxy)phosphanyloxy-2-methyloxan-3-yl] acetate 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 dibenzylphosphoryl 2,3,4-tri-O-acetyl-L-fucoside
  参考文献：
  名称：

  Sim, Mui Mui; Kondo, Hirosato; Wong, Chi-Huey, Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2260 - 2267

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-fucopyranose 在 1H-1,2,4-三唑 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(2S,3R,4R,5S)-4,5-diacetyloxy-6-bis(phenylmethoxy)phosphanyloxy-2-methyloxan-3-yl] acetate
  参考文献：
  名称：

  Sim, Mui Mui; Kondo, Hirosato; Wong, Chi-Huey, Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2260 - 2267

  摘要：

  DOI：

文献信息

• Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism
  作者：Hirosato Kondo、Shin Aoki、Yoshitaka Ichikawa、Randall L. Halcomb、Helena Ritzen、Chi-Huey Wong

  DOI：10.1021/jo00083a032

  日期：1994.2

  The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and accepters for the synthesis of several glycosides, including O-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are mixed. When the acceptor is treated with TMSOTf first, the glycosyl phosphite is activated by the resulting TfOH. The glycosyl phosphite can also be activated by TMSOTf directly. The best result is, however, to mix the acceptor and TMSOTf first, followed by addition of the glycosyl phosphite.
• Efficient chemical synthesis of GDP-fucose
  作者：Yoshitaka Ichikawa、Mui Mui Sim、Chi Huey Wong

  DOI：10.1021/jo00036a036

  日期：1992.5
• US5514784A
  申请人：——

  公开号：US5514784A

  公开（公告）日：1996-05-07
• US5597906A
  申请人：——

  公开号：US5597906A

  公开（公告）日：1997-01-28
• US5854391A
  申请人：——

  公开号：US5854391A

  公开（公告）日：1998-12-29