(2S,3R)-1-<(tert-butyldimethylsilyl)oxy>-2-methylhex-5-en-3-ol | 106318-21-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R)-1-<(tert-butyldimethylsilyl)oxy>-2-methylhex-5-en-3-ol
• 英文别名: (2S,3R)-1-(tert-butyldimethylsilyloxy)-2-methylhex-5-en-3-ol；(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-2-methylhex-5-en-3-ol；(2S,3R)-1-[tert-butyl(dimethyl)silyl]oxy-2-methylhex-5-en-3-ol
• CAS: 106318-21-2
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: BGRZRKHPNBYWOY-NWDGAFQWSA-N

物化性质

• 沸点：
  283.3±33.0 °C(Predicted)
• 密度：
  0.877±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-<(tert-butyldimethylsilyl)oxy>-2-methylhex-5-en-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-2-methylhex-5-en-2,3-diol
  参考文献：
  名称：

  Asymmetric synthesis using tartrate ester modified allylboronates. 2. Single and double asymmetric reactions with alkoxy-substituted aldehydes

  摘要：

  DOI：

  10.1021/jo00300a032
• 作为产物：
  描述：

  (2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal 、 (3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到(2S,3R)-1-<(tert-butyldimethylsilyl)oxy>-2-methylhex-5-en-3-ol
  参考文献：
  名称：

  A More Comprehensive and Highly Practical Solution to Enantioselective Aldehyde Crotylation

  摘要：

  The enantioselective crotylation of aldehydes with 1,2-diaminochlorocrotylsilane reagents is effectively catalyzed by Sc(OTf)(3). The one significant limitation on the utility of these reagents - substrate scope - has thus been addressed. The net result is the most comprehensive and highly practical method for enantioselective aldehyde crotylation yet advanced.

  DOI：

  10.1021/ja200712f

文献信息

• Synthetic studies on the mycolactone core
  作者：Kwang-Seuk Ko、Matthew D. Alexander、Shaun D. Fontaine、James E. Biggs-Houck、James J. La Clair、Michael D. Burkart

  DOI：10.1039/c0ob00540a

  日期：——

  Two approaches are presented for the synthesis of the macrolide core of the mycolactone polyketides. The first intertwines ring closing metathesis (RCM) within a two-step Julia olefination protocol, while the second intercepts the optimized routes of Kishi, thereby providing formal access to the mycolactones.

  提出了两种方法来合成聚甲基丙烯酸内酯聚酮化合物的大环内酯核心。第一个在两步茱莉亚烯化协议中缠绕闭环复分解（RCM），而第二个则截取了Kishi的优化路线，从而提供了对Mycolactones的正式使用。
• Catalytic Enantioselective and Catalyst-Controlled Diastereofacial-Selective Additions of Allyl- and Crotylboronates to Aldehydes Using Chiral Brønsted Acids
  作者：Vivek Rauniyar、Dennis G. Hall

  DOI：10.1002/anie.200504432

  日期：2006.4.3
• N,N'-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide: An Improved Chiral Auxiliary for the Asymmetric Allylboration Reaction
  作者：William R. Roush、Paul T. Grover

  DOI：10.1021/jo00117a036

  日期：1995.6

  N,N-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide (8), synthesized by a simple four-step sequence from ethylenediamine and benzylidenetartaric acid, was designed in anticipation that the derived allylboronates 9-11 would display enhanced reactivity owing to the inductive effect of the N-trifluoroethyl substituents that would increase the Lewis acidity of the boron atom of the B-allyl-1,3,2-dioxaborolanes. Reagents 9-11 were synthesized by transesterification of 8 with the crystalline and easily purified allylboronate diethanolamine complexes 13, 19, and 25. Allylboronate 9 is ca. 100-fold more reactive than 6 and is also substantially more useful than the previously reported allyboronate 4, which suffers from very poor solubility in toluene at -78 degrees C. Most importantly, allylboronates 9-11 are significantly more enantioselective than the parent tartrate allylboronates 1-3 and rank among the most highly enantioselective allylboron reagents yet reported. Reactions of 9-11 with aldehydes are performed in THF at- -78 or -55 degrees C for 5-12 h periods. The enantioselectivity realized in reactions with achiral aldehydes is 92-95% ee (Table 2), and excellent diastereoselectivity is achieved in double asymmetric reactions with chiral aldehydes 15a, 15b, and 33 (Tables 3 and 4). For example, 16 and 28 are now available with a minimum selectivity of 92% from reactions of 15a and 15b with allylboronate 9, while the crotylboration products 29, 30, and 31 are available with a minimum selectivity of 90% (usually greater than or equal to 95%) from reactions of 15a and 15b with crotylboronates 10 and 11; the fourth isomer, 32a, is available with 83% selectivity. Chiral reagents 9-11 thus appear well suited for application to complex problems in organic synthesis.
• ROUSH, WILLIAM R.;HOONG, LEE K.;PALMER, MICHELLE A. J.;STRAUB, JULIE A.;P+, J. ORG. CHEM., 55,(1990) N3, C. 4117-4126
  作者：ROUSH, WILLIAM R.、HOONG, LEE K.、PALMER, MICHELLE A. J.、STRAUB, JULIE A.、P+

  DOI：——

  日期：——
• ROUSH W. R.; PALKOWITZ A. D.; PALMER M. J., J. ORG. CHEM., 52,(1987) N 2, 316-318
  作者：ROUSH W. R.、 PALKOWITZ A. D.、 PALMER M. J.

  DOI：——

  日期：——