tert-Butyldimethylsilyl 2-azido-2-deoxy-β-lactoside | 121865-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyldimethylsilyl 2-azido-2-deoxy-β-lactoside
• 英文别名: tert-butyldimethylsilyl 2-azido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-azido-6-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 121865-28-9
• 化学式: C₁₈H₃₅N₃O₁₀Si
• 分子量: 481.576
• InChiKey: CNRWRQUCBSTQLI-QCAINAQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.05
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  173
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-Butyldimethylsilyl 2-azido-2-deoxy-β-lactoside 在 三氯化铁 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.5h， 生成 tert-Butyldimethylsilyl O-(3,4-O-Isopropylidene-β-D-galactopyranosyl)-(1->4)-3-O-allyl-2-azido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Bommer, Rene; Kinzy, Willy; Schmidt, Richard R., Liebigs Annalen der Chemie, 1991, # 5, p. 425 - 434

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-Butyldimethylsilyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosid 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以89%的产率得到tert-Butyldimethylsilyl 2-azido-2-deoxy-β-lactoside
  参考文献：
  名称：

  Jung, Karl-Heinz; Hoch, Monika; Schmidt, Richard R., Liebigs Annalen der Chemie, 1989, p. 1099 - 1106

  摘要：

  DOI：

文献信息

• Regioselective lipase acylation as a useful tool for separation and selective protection of β-d-Gal(1→4)-d-GlcNAc and β-d-Gal(1→3)-d-GlcNAc disaccharides
  作者：Barbara La Ferla、Luigi Lay、Giovanni Russo、Luigi Panza

  DOI：10.1016/s0957-4166(00)00342-6

  日期：2000.9

  Supported lipase from Candida antarctica (Chirazyme((R))) was employed for a regioselective protection of the 2-azido derivatives 1 and 2, synthetic equivalents of beta-(D)-Gal(1 ->3)-(D)-GlcNAc and beta-(D)-Gal(1->4)-(D-)GlcNAc (N-acetyl lactosamine), respectively. The selectivity of the enzyme towards 1 and 2 was also exploited for an easy separation of the mixture of the two compounds obtained from a straightforward synthetic approach. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Glycosylation with highly reactive glycosyl donors: efficiency of the inverse procedure
  作者：Richard R. Schmidt、Alexander Toepfer

  DOI：10.1016/s0040-4039(00)92704-7

  日期：1991.7

  Alpha-Fucosylation with the reactive trichloroacetimidate 1 as donor and disaccharides 2 and 4 as acceptors led to a remarkable increase in yield under ''inverse conditions'', i.e. addition of the donor to an acceptor/catalyst solution. Thus, acceptor/catalyst complex formation enforcing the generation of the glycosylating species in the vicinity of the acceptor is favored yielding building blocks for antigen determinant synthesis
• Jung, Karl-Heinz; Hoch, Monika; Schmidt, Richard R., Liebigs Annalen der Chemie, 1989, p. 1099 - 1106
  作者：Jung, Karl-Heinz、Hoch, Monika、Schmidt, Richard R.

  DOI：——

  日期：——
• Bommer, Rene; Kinzy, Willy; Schmidt, Richard R., Liebigs Annalen der Chemie, 1991, # 5, p. 425 - 434
  作者：Bommer, Rene、Kinzy, Willy、Schmidt, Richard R.

  DOI：——

  日期：——