[(3aR,4R,6R,7S,7aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-4-phenylmethoxy-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-7-yl] prop-2-enyl carbonate | 868367-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,4R,6R,7S,7aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-4-phenylmethoxy-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-7-yl] prop-2-enyl carbonate
• CAS: 868367-36-6
• 化学式: C₃₄H₃₉NO₈Si
• 分子量: 617.771
• InChiKey: RESMLZNTJXRHQU-JQWMYKLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6R,7S,7aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-4-phenylmethoxy-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-7-yl] prop-2-enyl carbonate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 [(2R,3S,4R,5R,6R)-5-amino-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：

  [(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 [(3aR,4R,6R,7S,7aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-oxo-4-phenylmethoxy-3,3a,4,6,7,7a-hexahydropyrano[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.