[2,2-di(tert-butyl)-7-(tert-butyldimethylsilanyloxy)-8-(tert-butyldiphenylsilanyloxy)-6-methylhexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl]acetic acid methyl ester | 849833-30-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [2,2-di(tert-butyl)-7-(tert-butyldimethylsilanyloxy)-8-(tert-butyldiphenylsilanyloxy)-6-methylhexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl]acetic acid methyl ester
• 英文别名: methyl 2-[(4aR,6S,7R,8S,8aR)-2,2-ditert-butyl-7-[tert-butyl(dimethyl)silyl]oxy-8-[tert-butyl(diphenyl)silyl]oxy-6-methyl-4a,7,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3,2]dioxasilin-6-yl]acetate
• CAS: 849833-30-3
• 化学式: C₄₀H₆₆O₇Si₃
• 分子量: 743.216
• InChiKey: GRYWQQZEXLCXDN-KEBILQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [2,2-di(tert-butyl)-7-(tert-butyldimethylsilanyloxy)-8-(tert-butyldiphenylsilanyloxy)-6-methylhexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl]acetic acid methyl ester 在 对甲苯磺酸 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 54.5h， 生成 [(2S,3R,4S,5R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-6-hydroxymethyl-2-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Substitution and Remote Protecting Group Influence on the Oxidation/Addition of α-Substituted 1,2-Anhydroglycosides:  A Novel Entry into C-Ketosides

  摘要：

  [GRAPHICS]C-Ketosides are valuable intermediates in chemical synthesis and as glycoside mimics. This manuscript describes the efficient generation of these substrates from alpha-alkyl-substituted glycals and an oxidative, C-C bond-forming sequence where the choice of C(3) protecting group was critical.

  DOI：

  10.1021/ol0501469
• 作为产物：
  描述：

  tert-butyl-[[(1R,3S,5R,6R,7R)-9,9-ditert-butyl-3-methyl-2,4,8,10-tetraoxa-9-silatricyclo[5.4.0.03,5]undecan-6-yl]oxy]-diphenylsilane 、 叔丁基二甲硅基三氟甲磺酸酯 、 1-(叔丁基二甲基硅氧基)-1-甲氧基乙烯 以 二氯甲烷 为溶剂， 反应 48.0h， 以77%的产率得到[2,2-di(tert-butyl)-7-(tert-butyldimethylsilanyloxy)-8-(tert-butyldiphenylsilanyloxy)-6-methylhexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl]acetic acid methyl ester
  参考文献：
  名称：

  Substitution and Remote Protecting Group Influence on the Oxidation/Addition of α-Substituted 1,2-Anhydroglycosides:  A Novel Entry into C-Ketosides

  摘要：

  [GRAPHICS]C-Ketosides are valuable intermediates in chemical synthesis and as glycoside mimics. This manuscript describes the efficient generation of these substrates from alpha-alkyl-substituted glycals and an oxidative, C-C bond-forming sequence where the choice of C(3) protecting group was critical.

  DOI：

  10.1021/ol0501469

文献信息

• Substitution and Remote Protecting Group Influence on the Oxidation/Addition of α-Substituted 1,2-Anhydroglycosides:  A Novel Entry into <i>C</i>-Ketosides
  作者：Scott W. Roberts、Jon D. Rainier

  DOI：10.1021/ol0501469

  日期：2005.3.1

  [GRAPHICS]C-Ketosides are valuable intermediates in chemical synthesis and as glycoside mimics. This manuscript describes the efficient generation of these substrates from alpha-alkyl-substituted glycals and an oxidative, C-C bond-forming sequence where the choice of C(3) protecting group was critical.