(S)-1-hydroxypent-4-en-2-yl benzoate | 206348-92-7

• 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: (S)-1-hydroxypent-4-en-2-yl benzoate
• 英文别名: [(2S)-1-hydroxypent-4-en-2-yl] benzoate
• CAS: 206348-92-7
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: KHDSGNDLCIESKE-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6S)-3,4,5-三苯甲酰氧基-6-(2,2,2-三氯亚氨代乙酰)氧基-四氢吡喃-2-基]甲基苯甲酸酯 、 (S)-1-hydroxypent-4-en-2-yl benzoate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以98%的产率得到(S)-2-benzoyloxy-4-pentene-1-yl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of glycosylated enantiomerically pure 4-pentene 1,2- and 1,3-diol derivatives

  摘要：

  1-Dimethylthexylsiloxy-2-chloroacetoxy-4 2 and 1-dimethylthexylsiloxy-3-chloroacetoxy-4-pentene 3 were saponified with Pseudomonas lipase to give (R)-1-dimethylthexylsiloxy-4-pentene-2-ol (ee=99%) and (S)-2 (ee=99%) and (S)-1-dimethylthexylsiloxy-4-pentene-3-ol (ee=99%) and (R)-3 (ee=98%), respectively. All enantiomers were chemically transformed into the corresponding enatiomerically pure 2-benzoyloxy-4-pentene-1-ols 8 and 3-benzoyloxy-4-pentene-1-ols 14, respectively. Mannosylation of (R)-8 and (S)-14 with 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl trichloroacetimidate afforded the corresponding mannopyranosides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00052-4
• 作为产物：
  描述：

  Benzoic acid (S)-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-but-3-enyl ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以97%的产率得到(S)-1-hydroxypent-4-en-2-yl benzoate
  参考文献：
  名称：

  Chemoenzymatic synthesis of glycosylated enantiomerically pure 4-pentene 1,2- and 1,3-diol derivatives

  摘要：

  1-Dimethylthexylsiloxy-2-chloroacetoxy-4 2 and 1-dimethylthexylsiloxy-3-chloroacetoxy-4-pentene 3 were saponified with Pseudomonas lipase to give (R)-1-dimethylthexylsiloxy-4-pentene-2-ol (ee=99%) and (S)-2 (ee=99%) and (S)-1-dimethylthexylsiloxy-4-pentene-3-ol (ee=99%) and (R)-3 (ee=98%), respectively. All enantiomers were chemically transformed into the corresponding enatiomerically pure 2-benzoyloxy-4-pentene-1-ols 8 and 3-benzoyloxy-4-pentene-1-ols 14, respectively. Mannosylation of (R)-8 and (S)-14 with 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl trichloroacetimidate afforded the corresponding mannopyranosides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00052-4

文献信息

• A novel chiral synthetic equivalent of glyoxal and its application to the asymmetric synthesis of O-protected α-hydroxy aldehydes
  作者：Lino Colombo、Marcello Di Giacomo

  DOI：10.1016/s0040-4039(99)00095-7

  日期：1999.3

  prepared in 83% yield from stannyloxazolidine 4. Grignard additions to the formyl group of compound 7 in the presence of Lewis acids afforded diastereomerically pure secondary carbinols 8. Protection of the hydroxyl group and unmasking of the oxazolidine ring gave O-protected α-hydroxy aldehydes 11, which were immediately reduced to the corresponding 1,2-diols 12.

  对映异构纯2-甲酰基的N-Boc-1,3-恶唑烷7在83％的产率制备从stannyloxazolidine 4。在路易斯酸的存在下，将格利雅（Grignard）加成化合物7的甲酰基，得到非对映体纯的仲甲醇8。羟基的保护和恶唑烷环的未掩蔽得到O保护的α-羟基醛11，将其立即还原为相应的1,2-二醇12。
• Diphenylprolinol silyl ether as a catalyst in an asymmetric, catalytic and direct α-benzoyloxylation of aldehydes
  作者：Hiroaki Gotoh、Yujiro Hayashi

  DOI：10.1039/b902287b

  日期：——

  Diphenylprolinol silyl ether was found to promote asymmetric, catalytic and direct α-benzoyloxylation of aldehydes with benzoyl peroxide to afford oxidized products in good yields with excellent enantioselectivity.

  研究发现，二苯基脯氨醇硅基醚可促进醛与过氧化苯甲酰的不对称、催化和直接δ-苯甲酰氧基化反应，从而以良好的收率和优异的对映选择性得到氧化产物。
• Kano, Taichi; Mii, Haruka; Maruoka, Keiji, Journal of the American Chemical Society, 2009, vol. 131, p. 3450 - 3451
  作者：Kano, Taichi、Mii, Haruka、Maruoka, Keiji

  DOI：——

  日期：——
• Organocatalytic α-oxybenzoylation of aldehydes
  作者：Matti J.P. Vaismaa、Sze Chak Yau、Nicholas C.O. Tomkinson

  DOI：10.1016/j.tetlet.2009.03.082

  日期：2009.7

  A simple method for the asymmetric alpha-oxybenzoylation of aldehydes is presented. Treatment of a series of aldehydes with benzoyl peroxide in the presence of a MacMillan imidazolidinone leads directly to the alpha-oxybenzoylated product with excellent levels of asymmetric induction. (C) 2009 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of glycosylated enantiomerically pure 4-pentene 1,2- and 1,3-diol derivatives
  作者：Frank Bien、Thomas Ziegler

  DOI：10.1016/s0957-4166(98)00052-4

  日期：1998.3

  1-Dimethylthexylsiloxy-2-chloroacetoxy-4 2 and 1-dimethylthexylsiloxy-3-chloroacetoxy-4-pentene 3 were saponified with Pseudomonas lipase to give (R)-1-dimethylthexylsiloxy-4-pentene-2-ol (ee=99%) and (S)-2 (ee=99%) and (S)-1-dimethylthexylsiloxy-4-pentene-3-ol (ee=99%) and (R)-3 (ee=98%), respectively. All enantiomers were chemically transformed into the corresponding enatiomerically pure 2-benzoyloxy-4-pentene-1-ols 8 and 3-benzoyloxy-4-pentene-1-ols 14, respectively. Mannosylation of (R)-8 and (S)-14 with 2,3,4,6-tetra-O-benzoyl-a-D-mannopyranosyl trichloroacetimidate afforded the corresponding mannopyranosides. (C) 1998 Elsevier Science Ltd. All rights reserved.