N-[(3R,4R,5S,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide | 805245-09-4

• 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: N-[(3R,4R,5S,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide
• 英文别名: N-[(3R,4R,5S,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxooxan-3-yl]acetamide
• CAS: 805245-09-4
• 化学式: C₃₆H₅₉NO₆Si₃
• 分子量: 686.124
• InChiKey: IYUIWKNVPJOACU-FEFKUCBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.77
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(3R,4R,5S,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide 在 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：

  1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose 在 Ra-Ni 碘苯二乙酸 、 sodium acetate 、 mercury(II) trifluoroacetate 、 叠氮化四丁基铵 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-[(3R,4R,5S,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-tetrahydro-pyran-3-yl]-acetamide
  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

文献信息

• 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.