(3aR,4S,6R,7S,7aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-4-p-tolylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one | 868367-32-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3aR,4S,6R,7S,7aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-4-p-tolylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one
• CAS: 868367-32-2
• 化学式: C₃₀H₃₅NO₅SSi
• 分子量: 549.763
• InChiKey: SLNOWDHEHAZYHX-FXGKLIOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aR,4S,6R,7S,7aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-4-p-tolylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one 在 吡啶 、 4-二甲氨基吡啶 、 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
• 作为产物：
  描述：

  (3aR,4S,6R,7S,7aR)-7-hydroxy-6-(hydroxymethyl)-4-(4-methylphenyl)sulfanyl-3,3a,4,6,7,7a-hexahydropyrano[3,4-d][1,3]oxazol-2-one 、 叔丁基二苯基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(3aR,4S,6R,7S,7aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-4-p-tolylsulfanyl-tetrahydro-pyrano[3,4-d]oxazol-2-one
  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