[(4S)-4,5-dihydroxypentyl] 4-methoxybenzoate | 1059187-44-8

• 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: [(4S)-4,5-dihydroxypentyl] 4-methoxybenzoate
• CAS: 1059187-44-8
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: RBHQYLJJTHLRBA-NSHDSACASA-N

物化性质

• 沸点：
  429.7±40.0 °C(predicted)
• 密度：
  1.195±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 [(4S)-4,5-dihydroxypentyl] 4-methoxybenzoate 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-4,5-bis((tert-butyldimethylsilyl)oxy)pent-1-yl 4-methoxybenzoate
  参考文献：
  名称：

  Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides

  摘要：

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.028
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 在 4-二甲氨基吡啶 、 potassium osmate(VI) 、 (DHQD)2PYDZ 、 potassium carbonate 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 5.0h， 生成 [(4S)-4,5-dihydroxypentyl] 4-methoxybenzoate
  参考文献：
  名称：

  The application of a mechanistic model leads to the extension of the Sharpless asymmetric dihydroxylation to allylic 4-methoxybenzoates and conformationally related amine and homoallylic alcohol derivatives.

  摘要：

  The scope and utility of the Sharpless asymmetric dihydroxylation has been expanded to include the use of allylic 4-methoxybenzoates as precursors of a wide variety of substituted chiral glycerol derivatives. The allylic 4-methoxybenzoyl group was found to be superior to other allylic alcohol protecting groups with respect to both yield and enantiomeric purity of the product. For example, asymmetric dihydroxylation of allyl 4-methoxybenzoate (6a) using the (DHQD)(2)PYDZ . OsO4 (1 . OsO4) catalyst system affords (S)-3-(4-methoxybenzoyloxy)-1,2-propanediol (7a) in >99% yield and 98% ee. The 4-methoxybenzoates of a variety of other allylic alcohols also serve as excellent substrates, in contrast to the parent alcohols themselves. The efficient asymmetric dihydroxylation of homoallylic 4-methoxyphenyl ethers (12a and 15), allyl 9-fluorenimine (18b), bis(homoallyl) 4-methoxybenzoate (14) and other structurally related substrates is also described. This methodology was developed under mechanistic guidance from the transition state model advanced earlier by us for the bis-cinchona alkaloid catalyzed asymmetric dihydroxylation reaction. The 4-methoxybenzoyl group functions not only to selectively protect one of the hydroxy groups of the product triol for subsequent synthetic manipulation but also to provide an extended binding group that participates in hydrophobic and aryl-aryl interactions with the U-shaped binding pocket of the (DHQD)(2)PYDZ . OsO4 catalyst (1 . OsO4), thereby enhancing enantioselectivity.

  DOI：

  10.1021/ja00149a003

文献信息

• Improved enantioselective dihydroxylation of bishomoallylic alcohol derivatives using a mechanistically inspired bis-cinchona alkaloid catalyst
  作者：E.J. Corey、Mark C. Noe、Alice Y. Ting

  DOI：10.1016/0040-4039(96)00163-3

  日期：1996.3

  The catalytic dihydroxylation of p-methoxybenzoate esters of various bishomoallylic alcohols proceeds with excellent enantioselectivity and, in the case of diolefins, with imporved regioselectivity using a designed catalyst that incorporates an N-anthracenylmethyl group to enhance catalyst-substrate binding interactions.

  各种双烯丙基烯丙醇的对甲氧基苯甲酸酯的催化二羟基化反应具有出色的对映选择性，在二烯烃的情况下，使用设计的催化剂引入了改进的区域选择性，该催化剂结合了N-蒽基甲基以增强催化剂与底物的结合作用。
• The application of a mechanistic model leads to the extension of the Sharpless asymmetric dihydroxylation to allylic 4-methoxybenzoates and conformationally related amine and homoallylic alcohol derivatives.
  作者：E. J. Corey、Angel Guzman-Perez、Mark C. Noe

  DOI：10.1021/ja00149a003

  日期：1995.11

  The scope and utility of the Sharpless asymmetric dihydroxylation has been expanded to include the use of allylic 4-methoxybenzoates as precursors of a wide variety of substituted chiral glycerol derivatives. The allylic 4-methoxybenzoyl group was found to be superior to other allylic alcohol protecting groups with respect to both yield and enantiomeric purity of the product. For example, asymmetric dihydroxylation of allyl 4-methoxybenzoate (6a) using the (DHQD)(2)PYDZ . OsO4 (1 . OsO4) catalyst system affords (S)-3-(4-methoxybenzoyloxy)-1,2-propanediol (7a) in >99% yield and 98% ee. The 4-methoxybenzoates of a variety of other allylic alcohols also serve as excellent substrates, in contrast to the parent alcohols themselves. The efficient asymmetric dihydroxylation of homoallylic 4-methoxyphenyl ethers (12a and 15), allyl 9-fluorenimine (18b), bis(homoallyl) 4-methoxybenzoate (14) and other structurally related substrates is also described. This methodology was developed under mechanistic guidance from the transition state model advanced earlier by us for the bis-cinchona alkaloid catalyzed asymmetric dihydroxylation reaction. The 4-methoxybenzoyl group functions not only to selectively protect one of the hydroxy groups of the product triol for subsequent synthetic manipulation but also to provide an extended binding group that participates in hydrophobic and aryl-aryl interactions with the U-shaped binding pocket of the (DHQD)(2)PYDZ . OsO4 catalyst (1 . OsO4), thereby enhancing enantioselectivity.
• Total synthesis of (4S,10R)-4-hydroxy-10-methyl-11-oxododec-2-en-1,4-olide and related bioactive marine butenolides
  作者：Wei-Min Dai、Lei Shi、Yannian Li

  DOI：10.1016/j.tetasy.2008.06.028

  日期：2008.7

  Marine-derived microorganisms produce structurally diverse butenolides possessing a variety of bioactivities. Described here is the total synthesis of (4S, 10R)-4-hydroxy-10-nnethyl-11-oxododec-2-en-1,4-olide and a related butenolide containing anti stereochemistry at C10-C11. A three-module coupling strategy has been established for synthesis of the stereoisomers of the naturally Occurring butenolides by assembling the C3-C7 and C9-C12 fragments via double alkylation of a 1,3-dithiane. The C10-C11 stereochemistry could be easily controlled by an asymmetric aldol condensation, while the butenolide unit was efficiently constructed according to the ring-closing metathesis protocol. (C) 2008 Elsevier Ltd. All rights reserved.