(1SR,2RS)-1-[(1RS)-2-(benzyloxy)-1-methylethyl]-2-methylpropane-1,3-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1SR,2RS)-1-[(1RS)-2-(benzyloxy)-1-methylethyl]-2-methylpropane-1,3-diol
• 英文别名: (2S,3R,4R)-2,4-dimethyl-5-phenylmethoxypentane-1,3-diol
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: IWLHKVFTKXOSID-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1SR,2RS)-1-[(1RS)-2-(benzyloxy)-1-methylethyl]-2-methylpropane-1,3-diol 在 Raney Ni(W-2) 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 草酰氯 、 氢气 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 176.67h， 生成 (2R,3R,4S)-1-tert-butyldimethylsilyloxy-3-(3,4-dimethoxybenzyloxy)-2,4,6,8-tetramethylnon-6-en-5-one
  参考文献：
  名称：

  Synthetic study of (9S)-9-dihydroerythronolide A via Wittig-Horner coupling of C1-C6 and C7-C15 segments.

  摘要：

  作为一项旨在实现（9S）-9-二氢红诺苷A全合成研究的一部分，进行了C7-C15片段（2S, 3R, 4S, 5R, 6R, 7R）-3, 5-异丙叉二氧-7-（4-甲氧基苄氧基）-6-甲氧基甲氧基-2, 4, 6-三甲基壬醛（由C9-C15三醇合成）与C1-C6片段二乙基（2RS, 4S, 5R, 6R）-6-叔丁基二甲基硅氧基-4-（3, 4-二甲氧基苄氧基）-2-氧代-1, 3, 5-三甲基己基膦酸酯（由C1-C5二醇合成）的Wittig-Horner偶联反应，合成了C1-C15烯酮，尽管产率较低。

  DOI：

  10.1248/cpb.37.1160
• 作为产物：
  描述：

  S-tert-butyl (2R,3S,4R)-3-hydroxy-2,4-dimethyl-5-phenylmethoxypentanethioate 生成 (1SR,2RS)-1-[(1RS)-2-(benzyloxy)-1-methylethyl]-2-methylpropane-1,3-diol
  参考文献：
  名称：

  GENNARI, C.;BERETTA, M. G.;BERNARDI, A.;MORO, G.;SCOLASTICO, C.;TODESCHIN+, TETRAHEDRON, 1986, 42, N 3, 893-909

  摘要：

  DOI：

文献信息

• Synthesis of Stereotriads by Oxymercuration of Substituted Cyclopropylcarbinols
  作者：Janine Cossy、Nicolas Blanchard、Christophe Meyer

  DOI：10.1021/ol0162365

  日期：2001.8.9

  Cyclopropylcarbinol derivatives bearing an adjacent methyl-substituted stereocenter and a remote beta-hydroxy group protected as a pivalate underwent anchimerically assisted regio- and diastereoselective oxymercurations, affording after reductive demercuration, an access to stereotriads.

  [结构：见正文]带有相邻甲基取代的立体中心和被保护为新戊酸酯的远端β-羟基的环丙基甲醇衍生物进行了手性辅助的区域和非对映选择性的氧化汞反应，在还原脱汞后可得到立体三单元。
• Alternative syntheses of the C9-C15 and C1-C5 segments of erythronolide A via regio- and stereo-selective reductive ring opening of 2,3-epoxy alcohols.
  作者：Hitoshi TONE、Masataka HIKOTA、Tatsuo HAMADA、Takao NISHI、Yuji OIKAWA、Osamu YONEMITSU

  DOI：10.1248/cpb.37.1155

  日期：——

  Improved syntheses are described of two segments required for the total synthesis of (9S)-9-dihydroerythronolide. A, i.e., (2S, 3R, 4S, 5R)-2, 4-dimethyl-5-(4-methoxybenzyloxy)heptane-1, 3, 4-triol corresponding to the C9-C15 subunit and (2S, 3R, 4R)-5-benzyloxy-2, 3-dimethylpentane-1, 4-diol corresponding to the C1-C5 subunit, via regio- and stereo-selective reduction of 2, 3-epoxy alcohols.

  改进了合成方法，以获得总合成（9S）-9-二氢红霉素所需的两个片段。A，即（2S，3R，4S，5R）-2, 4-二甲基-5-(4-甲氧基苄氧)庚烷-1, 3, 4-三醇，对应于C9-C15亚单位；（2S，3R，4R）-5-苄氧-2, 3-二甲基戊烷-1, 4-二醇，对应于C1-C5亚单位，通过区域和立体选择性还原2, 3-环氧醇得到。
• Chiral synthesis of polyketide-derived natural products. Part 5. Synthesis of a chiral segment corresponding to the C-1—C-5 unit of erythromycin A from<scp>D</scp>-glucose
  作者：Yuji Oikawa、Takao Nishi、Osamu Yonemitsu

  DOI：10.1039/p19850000019

  日期：——

  As a right-hand segment with three consecutive chiral centres corresponding to the C-1—C-5 unit of erythromycin A (1), (2S,3R,4S)-3,5-isopropylidenedioxy-2,4-dimethylpentanal (32) was synthesized from D-glucose (5) by application of MPM (4-methoxybenzyl) protection for an hydroxy function and some fairly stereoselective reactions, hydroboration and hydrogenation.

  作为右侧部分，具有三个连续的手性中心，分别对应于红霉素A（1），（2 S，3 R，4 S）-3,5-异丙基二烯基-2,4-的C-1–C-5单元通过应用MPM（4-甲氧基苄基）保护羟基功能和一些相当立体选择性的反应，硼氢化和氢化反应，由D-葡萄糖（5）合成了二甲基戊醛（32）。
• Synthesis of polypropionate subunits from cyclopropanes
  作者：Magali Defosseux、Nicolas Blanchard、Christophe Meyer、Janine Cossy

  DOI：10.1016/j.tet.2005.05.099

  日期：2005.8

  The oxymercuration-reductive demercuration of several cyclopropanealkanol or their derivatives bearing adjacent stereocenters has been investigated in order to synthesize polypropionate subunits. The crucial importance of the ester protecting group for the remote oxygenated moieties on the mechanism and the stereochemical outcome of these reactions has been rationalized. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00030a036

  日期：1992.2

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.