allyl 6-O-(tert-butyldiphenylsilyl)-D-galactopyranosyl-β-(1,4)-2-acetamido-2-deoxy-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside | 144002-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-O-(tert-butyldiphenylsilyl)-D-galactopyranosyl-β-(1,4)-2-acetamido-2-deoxy-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside
• 英文别名: TBDPS(-6)Gal(b1-4)[TBDPS(-6)]GlcNAc(b)-O-allyl；N-[(2R,3R,4R,5S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-[(2S,3R,4S,5R,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-2-prop-2-enoxyoxan-3-yl]acetamide
• CAS: 144002-27-7
• 化学式: C₄₉H₆₅NO₁₁Si₂
• 分子量: 900.226
• InChiKey: LWOBXAJEOOWWRV-ISZYKFAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  63
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  165
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  allyl 6-O-(tert-butyldiphenylsilyl)-D-galactopyranosyl-β-(1,4)-2-acetamido-2-deoxy-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside 、 Benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-O-(dibenzylphosphityl)-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以48%的产率得到Allyl -(2,3)-6-O-(tert-butyldiphenylsilyl)-β-D-galactosyl-(1,4)-2-acetamido-2-deoxy-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism

  摘要：

  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.

  DOI：

  10.1021/jo00083a032
• 作为产物：
  描述：

  allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 、 β-半乳糖苷酶 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以7%的产率得到TBDPS(-3)[TBDPS(-6)]Gal(b1-4)[TBDPS(-6)]GlcNAc(b)-O-allyl
  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

• Kondo, Hirosato; Ichikawa, Yoshitaka; Wong, Chi-Huey, Journal of the American Chemical Society, 1992, vol. 114, # 22, p. 8748 - 8750
  作者：Kondo, Hirosato、Ichikawa, Yoshitaka、Wong, Chi-Huey

  DOI：——

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

  DOI：——

  日期：——
• 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.