(1R)-1-[(4R,5R)-5-[(1R)-1-hydroxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propan-1-ol | 159716-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-[(4R,5R)-5-[(1R)-1-hydroxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propan-1-ol
• CAS: 159716-51-5
• 化学式: C₁₁H₂₂O₄
• 分子量: 218.293
• InChiKey: DQTPSPALDJONJO-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(4R,5R)-5-[(1R)-1-hydroxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propan-1-ol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 (4R,5S,6S,7R)-5,6-O-(1-methylethylidene)-4,7-diethyl[1,3,2]dioxathiepane 2,2-dioxide
  参考文献：
  名称：

  由D-甘露糖醇合成手性羟基膦酸酯及其在不对称催化反应中的应用。

  摘要：

  手性羟基一膦3 [（2S，3S，4S，5S）-3,4-二羟基-2，5-二甲基-1-苯基膦烷]和双膦酸酯5a [1,2-双[（2S，3S，4S，5S） -3,4-二羟基-2,5-二甲基磷杂环戊烷基]苯]和5b [1,2-双[（2S，3S，4S，5S）-2,5-二乙基-3,4-二羟基磷杂环戊基]苯]从现成的D-甘露醇中以高收率获得。已经研究了在膦存在下保护和脱保护OH-基团的策略。当使用羟基膦作为催化剂时，在Baylis-Hillman反应中观察到速率加速。铑与手性双膦酸酯的络合物是高度对映选择性的催化剂，用于各种官能化烯烃（如脱氢氨基酸衍生物，衣康酸衍生物和烯酰胺）的不对称氢化。

  DOI：

  10.1021/jo000066c
• 作为产物：
  描述：

  甲基锂 、 1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 (1R)-1-[(4R,5R)-5-[(1R)-1-hydroxypropyl]-2,2-dimethyl-1,3-dioxolan-4-yl]propan-1-ol
  参考文献：
  名称：

  Synthesis, Characterization, and Applicability of Neutral Polyhydroxy Phospholane Derivatives and Their Rhodium(I) Complexes for Reactions in Organic and Aqueous Media

  摘要：

  Two different protocols for the preparation of water-soluble, enantiomerically pure polyhydroxybisphospholanes from acid-labile acetal and tert-butyldimethylsilyl-protected derivatives are reported. These procedures circumvent two of the commonly encountered limitations in the synthesis of these potentially important ligands: (a) formation of phosphonium salts from the highly basic phosphine under acidic conditions, and (b) the need to start with preformed, fully protected cationic metal complex. Thus, cationic Rh complexes of these ligands have been prepared in a separate step, and they have been found to be excellent catalysts for organic and aqueous phase hydrogenation of dehydroamino acids. The viability of catalyst recovery has been demonstrated in three different systems, including two cases where > 99% ee can be achieved under recycling conditions.

  DOI：

  10.1021/ja011500a

文献信息

• Asymmetric catalysis based on chiral phospholanes and hydroxyl phospholanes
  申请人：The Penn State Research Foundation

  公开号：US06727377B2

  公开（公告）日：2004-04-27

  Chiral phosphine ligands derived from chiral natural products including D-mannitol and tartaric acid. The ligands contain one or more 5-membered phospholane rings with multiple chiral centers, and provide high stereoselectivity in asymmetric reactions.

  来自手性天然产物的手性膦配体，包括D-甘露醇和酒石酸。这些配体含有一个或多个含有多个手性中心的5元磷环，可在不对称反应中提供高立体选择性。
• GAWRONSKI, JACEK;GAWRONSKA, KRYSTYNA, CARBOHYDR. RES., 206,(1990) N, C. 41-53
  作者：GAWRONSKI, JACEK、GAWRONSKA, KRYSTYNA

  DOI：——

  日期：——
• Synthesis of Chiral Hydroxyl Phospholanes from <scp>d</scp>-mannitol and Their Use in Asymmetric Catalytic Reactions
  作者：Wenge Li、Zhaoguo Zhang、Dengming Xiao、Xumu Zhang

  DOI：10.1021/jo000066c

  日期：2000.6.1

  Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis-Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino

  手性羟基一膦3 [（2S，3S，4S，5S）-3,4-二羟基-2，5-二甲基-1-苯基膦烷]和双膦酸酯5a [1,2-双[（2S，3S，4S，5S） -3,4-二羟基-2,5-二甲基磷杂环戊烷基]苯]和5b [1,2-双[（2S，3S，4S，5S）-2,5-二乙基-3,4-二羟基磷杂环戊基]苯]从现成的D-甘露醇中以高收率获得。已经研究了在膦存在下保护和脱保护OH-基团的策略。当使用羟基膦作为催化剂时，在Baylis-Hillman反应中观察到速率加速。铑与手性双膦酸酯的络合物是高度对映选择性的催化剂，用于各种官能化烯烃（如脱氢氨基酸衍生物，衣康酸衍生物和烯酰胺）的不对称氢化。
• Synthesis, Characterization, and Applicability of Neutral Polyhydroxy Phospholane Derivatives and Their Rhodium(I) Complexes for Reactions in Organic and Aqueous Media
  作者：T. V. RajanBabu、Yuan-Yong Yan、Seunghoon Shin

  DOI：10.1021/ja011500a

  日期：2001.10.1

  Two different protocols for the preparation of water-soluble, enantiomerically pure polyhydroxybisphospholanes from acid-labile acetal and tert-butyldimethylsilyl-protected derivatives are reported. These procedures circumvent two of the commonly encountered limitations in the synthesis of these potentially important ligands: (a) formation of phosphonium salts from the highly basic phosphine under acidic conditions, and (b) the need to start with preformed, fully protected cationic metal complex. Thus, cationic Rh complexes of these ligands have been prepared in a separate step, and they have been found to be excellent catalysts for organic and aqueous phase hydrogenation of dehydroamino acids. The viability of catalyst recovery has been demonstrated in three different systems, including two cases where > 99% ee can be achieved under recycling conditions.