(1R,2R,6R,7R)-4,4-dimethyl-3,5,10-trioxatricyclo[5.2.1.02,6]decan-8-one | 84121-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,6R,7R)-4,4-dimethyl-3,5,10-trioxatricyclo[5.2.1.02,6]decan-8-one
• CAS: 84121-00-6；84472-27-5；118244-86-3；118244-88-5
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: VLGKFQNFQGLVGQ-CWKFCGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,6R,7R)-4,4-dimethyl-3,5,10-trioxatricyclo[5.2.1.02,6]decan-8-one 生成 (-)-2-<<(tert-butyl)dimethylsilyl>oxy>-5,6-exo-(isopropylidenedioxy)-7-oxabicyclo<2.2.1>hept-2-ene
  参考文献：
  名称：

  JEGANATHAN, SURULIAPPA;VOGEL, PIERRE, J. ORG. CHEM., 56,(1991) N, C. 1139-1142

  摘要：

  DOI：
• 作为产物：
  描述：

  [(1R,2R,6R,7R,8S)-8-cyano-4,4-dimethyl-3,5,10-trioxatricyclo[5.2.1.02,6]decan-8-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate 生成 (1R,2R,6R,7R)-4,4-dimethyl-3,5,10-trioxatricyclo[5.2.1.02,6]decan-8-one
  参考文献：
  名称：

  WAGNER, JURGEN;VIEIRA, ERIC;VOGEL, PIERRE, HELV. CHIM. ACTA, 71,(1988) N 3, 624-630

  摘要：

  DOI：

文献信息

• Total Synthesis ofL-Allose,L-Talose, and derivatives.
  作者：Yves Auberson、Pierre Vogel

  DOI：10.1002/hlca.19890720212

  日期：1989.3.15

  (1S, 4R, 5S, 6S)-5-exo, 6-exo-(Isopropylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one ((−)-1) was transformed with high stereoselectivity to L-allose. Similarly, enantiomer (+)-1 was transformed into L-talose. The ketones (+)-1 and (−)-1 were derived from furan and 1-cyanovinyl (1S)-camphanate and 1-cyanovinyl (1R)-camphanate, respectively.

  将（1 S，4 R，5 S，6 S）-5- exo，6- exo-（异丙二烯二氧基）-7-氧杂双环[2.2.1]庚-2--2-（（-）- 1）转化为高对L-阿洛糖的立体选择性。类似地，对映异构体（+）- 1被转化为L-塔洛糖。酮（+1）-1和（-1）-1分别来自呋喃和1-氰基乙烯基（1S）-樟脑酸酯和1-氰基乙烯基（1R）-樟脑酸酯。
• Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives (naked sugars) as synthetic intermediates. 18. Synthesis of .alpha.-(1.fwdarw.2)-, .alpha.-(1.fwdarw.3)-, .alpha.-(1.fwdarw.4)-, and .alpha.-(1.fwdarw.5)-C-linked disaccharides through 2,3,4,6-tetra-O-acetylglucopyranosyl radical additions to 3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one derivatives
  作者：R. Mampuya Bimwala、Pierre Vogel

  DOI：10.1021/jo00033a032

  日期：1992.3

  The ''naked sugar'' (+)-1 (1R,2S,4R)-2-cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1S')-camphanate) has been converted into (+)-(1R,4R,5R,6R)-3-methylidene-5-exo,6-exo(isopropylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one ((+)-3) and (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one ((-)-26). Reductive addition of 2,3,4,6-tetra-O-acetylglucopyranosyl radical onto (+)-3 and (-)-26 were highly stereoselective giving exclusively 3-endo-(glucosylmethyl)-7-oxabicyclo[2.2.1]heptan-2-one derivatives. The anomeric selectivity (alpha-C-glucoside vs beta-C-glucoside) was 5.5:1 with (+)-3 and 8:1 with (-)-26. The C-glucosides so-obtained were transformed into alpha-(1 --> 2)-, alpha-(1 --> 3)-, alpha-(1 --> 4)-, and alpha-(1 --> 5)-C-linked disaccharide derivatives which combine alpha-D-glucopyranose with L-altro-hexonolactone, L-manno-hexonolactone, L-mannose, and L-(talo-hexofuranosid)uronic acid, respectively.
• JEGANATHAN, SURULIAPPA;VOGEL, PIERRE, TETRAHEDRON LETT., 31,(1990) N2, C. 1717-1720
  作者：JEGANATHAN, SURULIAPPA、VOGEL, PIERRE

  DOI：——

  日期：——
• JEGANATHAN, SURULIAPPA;VOGEL, PIERRE, J. ORG. CHEM., 56,(1991) N, C. 1139-1142
  作者：JEGANATHAN, SURULIAPPA、VOGEL, PIERRE

  DOI：——

  日期：——
• WAGNER, JURGEN;VIEIRA, ERIC;VOGEL, PIERRE, HELV. CHIM. ACTA, 71,(1988) N 3, 624-630
  作者：WAGNER, JURGEN、VIEIRA, ERIC、VOGEL, PIERRE

  DOI：——

  日期：——