tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside | 136505-41-4

• 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: tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3R,4R,5S,6R)-3-azido-2-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-6-(phenylmethoxymethyl)oxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 136505-41-4
• 化学式: C₃₃H₄₉N₃O₁₄Si
• 分子量: 739.849
• InChiKey: SRILRPRVZKACAA-APGCWEHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  220.34
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1<*>4)-O-<(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Toepfer, Alexander; Schmidt, Richard R., Journal of Carbohydrate Chemistry, 1993, vol. 12, # 7, p. 809 - 822

  摘要：

  DOI：
• 作为产物：
  描述：

  tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid 在 盐酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 1.33h， 生成 tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Toepfer, Alexander; Schmidt, Richard R., Journal of Carbohydrate Chemistry, 1993, vol. 12, # 7, p. 809 - 822

  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.
• Toepfer, Alexander; Kinzy, Willy; Schmidt, Richard R., Liebigs Annalen der Chemie, 1994, # 5, p. 449 - 464
  作者：Toepfer, Alexander、Kinzy, Willy、Schmidt, Richard R.

  DOI：——

  日期：——
• 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