[(3aR,4S,6R,7S,7aR)-3-acetyl-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(4-methylphenyl)sulfanyl-2-oxo-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] prop-2-enyl carbonate | 868367-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,4S,6R,7S,7aR)-3-acetyl-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(4-methylphenyl)sulfanyl-2-oxo-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] prop-2-enyl carbonate
• CAS: 868367-34-4
• 化学式: C₃₆H₄₁NO₈SSi
• 分子量: 675.875
• InChiKey: LZCFJMULVRHINH-UPYFENACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(3aR,4S,6R,7S,7aR)-3-acetyl-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(4-methylphenyl)sulfanyl-2-oxo-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] prop-2-enyl carbonate 在 锂硼氢 、 trifluoromethanesulfonic acid anhydride 、 1-piperidinyl benzyl sulfoxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(2R,3S,4R,5R,6R)-5-acetamido-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-6-phenylmethoxyoxan-3-yl] prop-2-enyl carbonate
  参考文献：
  名称：

  Chemoselective deprotection and functional group interconversion of ring-fused 2N,3O-oxazolidinones of N-acetyl-d-glucosamine

  摘要：

  These studies describe the chemoselective deprotection of trans-fused 2N,3O-oxazolidinone derivatives of N-acetyl-beta-D-glucosamine. Selective opening of the oxazolidinone ring or N-deacetylation without ring opening is demonstrated. Certain amines are shown to efficiently afford C-2 ureido sugars under mild conditions. This work demonstrates the high degree of chemoselective manipulation possible with ring-fused 2N,3O-oxazolidinone derivatives of N-acetyl-D-glucosamine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.013
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(3aR,4S,6R,7S,7aR)-3-acetyl-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-(4-methylphenyl)sulfanyl-2-oxo-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-7-yl] prop-2-enyl carbonate
  参考文献：
  名称：

  Chemoselective deprotection and functional group interconversion of ring-fused 2N,3O-oxazolidinones of N-acetyl-d-glucosamine

  摘要：

  These studies describe the chemoselective deprotection of trans-fused 2N,3O-oxazolidinone derivatives of N-acetyl-beta-D-glucosamine. Selective opening of the oxazolidinone ring or N-deacetylation without ring opening is demonstrated. Certain amines are shown to efficiently afford C-2 ureido sugars under mild conditions. This work demonstrates the high degree of chemoselective manipulation possible with ring-fused 2N,3O-oxazolidinone derivatives of N-acetyl-D-glucosamine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.013

文献信息

• Chemoselective deprotection and functional group interconversion of ring-fused 2N,3O-oxazolidinones of N-acetyl-d-glucosamine
  作者：Peng Wei、Robert J. Kerns

  DOI：10.1016/j.tetlet.2005.08.013

  日期：2005.10

  These studies describe the chemoselective deprotection of trans-fused 2N,3O-oxazolidinone derivatives of N-acetyl-beta-D-glucosamine. Selective opening of the oxazolidinone ring or N-deacetylation without ring opening is demonstrated. Certain amines are shown to efficiently afford C-2 ureido sugars under mild conditions. This work demonstrates the high degree of chemoselective manipulation possible with ring-fused 2N,3O-oxazolidinone derivatives of N-acetyl-D-glucosamine. (c) 2005 Elsevier Ltd. All rights reserved.