[(3aR,5R,6S,7R,7aR)-6,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-pyrano[3,2-d]thiazol-3a-yl]-acetic acid ethyl ester | 805245-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,5R,6S,7R,7aR)-6,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-pyrano[3,2-d]thiazol-3a-yl]-acetic acid ethyl ester
• 英文别名: ethyl 2-[(3aR,5R,6S,7R,7aR)-6,7-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-methyl-5,6,7,7a-tetrahydropyrano[3,2-d][1,3]thiazol-3a-yl]acetate
• CAS: 805245-17-4
• 化学式: C₄₀H₆₅NO₆SSi₃
• 分子量: 772.282
• InChiKey: PPWBUJBROOADLX-APWBIKNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.93
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6S,7R,7aR)-6,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-5,6,7,7a-tetrahydro-pyrano[3,2-d]thiazol-3a-yl]-acetic acid ethyl ester 在 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到((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：

  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 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.0h， 生成 [(3aR,5R,6S,7R,7aR)-6,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-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

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.