2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone | 336130-14-4

• 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: 2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone
• 英文别名: (3R,4R,5S,6R)-3-azido-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]oxan-2-one
• CAS: 336130-14-4
• 化学式: C₃₄H₅₅N₃O₅Si₃
• 分子量: 670.084
• InChiKey: XPVCWULKICFVMF-GKIKGMKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone 在 Ra-Ni 劳森试剂 、 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.0h， 生成 ((3aR,5R,6R,7R,7aR)-6,7-Dihydroxy-5-hydroxymethyl-2-methyl-5,6,7,7a-tetrahydro-pyrano[3,2-d]thiazol-3a-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  A fused GalNAc-thiazole from a singular and unanticipated fragmentation

  摘要：

  Attempted O-desilylation of an elaborated GalNAc-thiazoline t-butyl ester gave rise instead to a GalNAc-thiazole wherein the two-carbon acetate side chain has been severed by a process heretofore undescribed. The corresponding ether ester rearranged to a C-furanoside by a quite different pathway. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.091
• 作为产物：
  描述：

  3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactopyranose 在 4 A molecular sieve 、 sodium acetate 、 双(三甲基硅烷基)氨基钾 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.83h， 生成 2-azido-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactono-1,5-lactone
  参考文献：
  名称：

  构象约束的糖基化氨基酸的设计和合成。

  摘要：

  为了探究O-连接糖蛋白与各种酶和受体结合的构象要求，设计了两个构象约束的糖基化氨基酸2和3。通过分子建模发现类似物代表母体缀合物1的两个潜在的低能构象。提出了由D-半乳糖和L-蛋氨酸的聚合合成2和3。

  DOI：

  10.1021/jo001512z

文献信息

• New design concepts for constraining glycosylated amino acids
  作者：Jonathan W Lane、Randall L Halcomb

  DOI：10.1016/s0040-4020(01)00545-2

  日期：2001.7

  In an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, two constrained glycopeptides based on the alpha -N-acetylgalactosaminyl serine substructure were chosen for synthesis. These compounds representing one of the two possible gauche conformations of the D-serine and L-serine configurations of the parent substructure were successfully prepared in reasonable overall yield through a convergent strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Stereoselective Synthesis of Conformationally Constrained Glycosylated Amino Acids Using an Enzyme-Catalyzed Desymmetrization
  作者：Jonathan W. Lane、Randall L. Halcomb

  DOI：10.1021/jo020532t

  日期：2003.2.1

  As part of an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, constrained glycopeptides, compounds 2 and 3, based on the alpha-N-acetylgalactosaminyl serine substructure 1, were designed. In this paper we describe a stereoselective preparation of protected versions of these compounds. A pig liver esterase-catalyzed enzymatic desymmetrization of a diacetate substrate, 10, was employed as a key component in the synthesis.
• A fused GalNAc-thiazole from a singular and unanticipated fragmentation
  作者：Spencer Knapp、Benjamin Amorelli、George A. Doss

  DOI：10.1016/j.tetlet.2004.09.091

  日期：2004.11

  Attempted O-desilylation of an elaborated GalNAc-thiazoline t-butyl ester gave rise instead to a GalNAc-thiazole wherein the two-carbon acetate side chain has been severed by a process heretofore undescribed. The corresponding ether ester rearranged to a C-furanoside by a quite different pathway. (C) 2004 Elsevier Ltd. All rights reserved.
• Design and Synthesis of Conformationally Constrained Glycosylated Amino Acids
  作者：Jennifer L. Koviach、Mark D. Chappell、Randall L. Halcomb

  DOI：10.1021/jo001512z

  日期：2001.4.1

  To probe the conformational requirements of O-linked glycoproteins for binding to various enzymes and receptors, two conformationally constrained glycosylated amino acids, 2 and 3, were designed. The analogues were found to represent two potential low energy conformations of the parent conjugate, 1, by molecular modeling. A convergent synthesis of both 2 and 3 from D-galactose and L-methionine is presented

  为了探究O-连接糖蛋白与各种酶和受体结合的构象要求，设计了两个构象约束的糖基化氨基酸2和3。通过分子建模发现类似物代表母体缀合物1的两个潜在的低能构象。提出了由D-半乳糖和L-蛋氨酸的聚合合成2和3。