(R)-2-{[(tert-Butyl)diphenylsilyl]oxy}-1-phenylethanol | 129376-74-5

• 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: (R)-2-{[(tert-Butyl)diphenylsilyl]oxy}-1-phenylethanol
• 英文别名: (1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-phenylethanol
• CAS: 129376-74-5
• 化学式: C₂₄H₂₈O₂Si
• 分子量: 376.571
• InChiKey: DZGDTFPYSCICMK-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (R)-2-{[(tert-Butyl)diphenylsilyl]oxy}-1-phenylethanol 在 4-二甲氨基吡啶 、 molecular sieve 、 水 、 臭氧 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  2-取代的1 H Indole-3-ethanamines（= Tryptamines）的C-（烷氧羰基）甲亚胺的非对映选择性螺环化：基础研究。第五次有关吲哚，吲哚肾上腺素和吲哚啉的交流†

  摘要：

  Ç -型的（烷氧基羰基）formimines 15-18是从2-取代的色胺衍生的2，9，10，和11和用甲苯磺酰氯转化为类型三环3- spiroindoles 19-22（方案3）。研究了同手性烷氧基部分AD对该反应的立体化学结果的影响。以（-）-8-（苯基薄荷基-3-基）氧基（B）为纯手性助剂，观察到优异的非对映选择性。三轮车4，（2'R，3 S）-19B和（2'通过X射线分析确定S，3 R）20C，通过NOE和CD研究以及通过化学相关性确定其他化合物的结构。讨论了解释螺环化的空间过程的可能性。

  DOI：

  10.1002/hlca.19900730224
• 作为产物：
  描述：

  tert-butyl-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-phenylethoxy]-diphenylsilane 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到(R)-2-{[(tert-Butyl)diphenylsilyl]oxy}-1-phenylethanol
  参考文献：
  名称：

  On the chemoselectivity and mechanism of desilylation of tert-butyldimethylsilyl ethers with TMSOTf

  摘要：

  A modified literature procedure is presented for desilylating primary and secondary tert-butyldimethylsilyl ethers involving TMSOTf followed by breakdown of the bis-silyloxonium ion in methanol. The chemoselectivity of the process with respect to TBDPS, TIPS, MEM, ester, ketal, acetate, benzoate and NBoc functionalities has been evaluated, and a mechanism involving intermediacy of a transient tert-butyldimethylsilylium ion is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00523-7

文献信息

• Hyperbranched chiral catalysts for the asymmetric reduction of ketones with borane
  作者：Carsten Bolm、Nadine Derrien、Andreas Seger

  DOI：10.1039/a906258k

  日期：——

  Optically active dendritic amino alcohols catalyse the enantioselective borane reduction of ketones with good yields and high enantiomeric excesses.

  具有光学活性的树枝状氨基醇类化合物能够催化酮类化合物的手性硼氢还原反应，具有良好的产率和高对映选择性。
• Use of NaBH4/Me3SiCl in the β-hydroxysulfoximine-catalyzed enantioselective reduction of ketones
  作者：Carsten Bolm、Andreas Seger、Marcel Felder

  DOI：10.1016/s0040-4039(00)61455-7

  日期：1993.12

  The use of NaBH4/Me(3)SiCl in the beta-hydroxysulfoximine-catalyzed asymmetric reduction of ketones affords secondary alcohols in high yields with good enantioselectivities (up to 90% ee).
• Diastereoselective Synthesis of the Monosaccharide Kedarosamine and Incorporation in an Analogue of the Enediyne Kedarcidin Chromophore
  作者：Tatjana Vuljanic、Jan Kihlberg、Peter Somfai

  DOI：10.1021/jo971380i

  日期：1998.1.1

  Kedarcidin chromophore, as with most enediyne antitumor antibiotics, contains unusual monosaccharide moieties. Synthesis of one of these moieties, the 2,4,6-trideoxy-4-dimethylaminohexose kedarosamine, from D-threonine and incorporation into an analogue of kedarcidin chromophore (1) is described herein. Conversion of D-threonine into allyl ketone 7 and stereoselective reduction by using tetramethylammonium triacetoxyborohydride for intramolecular hydride delivery were key steps in the preparation of kedarosamine. A thioglycoside derivative of kedarosamine (12) was found to be less efficient as a glycosyl donor, whereas a 1-O-acetate (15) gave the desired alpha-glycoside exclusively in 60-80% yield when treated with borontrifluoride etherate. Use of a Cbz instead of a Fmoc protecting group for the C-4 amino group of kedarosamine was essential for the successful preparation of analogue 1. Finally, dimethylation of the amino group at C-4 of kedarosamine was found to require careful adjustment of the reaction conditions in order to avoid byproduct formation.
• FREUND, RALF;MAHBOOBI, SIAVOSH;NOACK, KLAUS;SCHONHOLZER, PETER;BERNAUER, +, HELV. CHIM. ACTA, 73,(1990) N, C. 439-454
  作者：FREUND, RALF、MAHBOOBI, SIAVOSH、NOACK, KLAUS、SCHONHOLZER, PETER、BERNAUER, +

  DOI：——

  日期：——
• On the chemoselectivity and mechanism of desilylation of tert-butyldimethylsilyl ethers with TMSOTf
  作者：Roger Hunter、Wolfgang Hinz、Philip Richards

  DOI：10.1016/s0040-4039(99)00523-7

  日期：1999.4

  A modified literature procedure is presented for desilylating primary and secondary tert-butyldimethylsilyl ethers involving TMSOTf followed by breakdown of the bis-silyloxonium ion in methanol. The chemoselectivity of the process with respect to TBDPS, TIPS, MEM, ester, ketal, acetate, benzoate and NBoc functionalities has been evaluated, and a mechanism involving intermediacy of a transient tert-butyldimethylsilylium ion is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.