^Ferrier, Robert J. Unsaturated Carbohydrates. Part 21. A Carboxylic Ring Closure of a Hex-5-enopyranoside Derivative. J. Chem. Soc., Perkin Trans. 1. 1979: 1455–1458. doi:10.1039/P19790001455.
^ 2.02.1Konstantinović, Stanimir; et al. The Ferrier rearrangement as the key step in the synthesis of C7–C16-alkyl 2,3-dideoxy glucosides from glucose and C7–C16-alkanols (PDF). J.Serb.Chem.Soc. 2001, 66 (8): 499–505 [2009-10-09]. （原始内容 (PDF)于2011-10-08）.
^Boga, S. B.; Balasubramanian, K. K. Indium trichloride catalyzed Ferrier rearrangement – facile synthesis of 2,3-unsaturated glycosides. Arkivoc. 2004: 87–102 [2009-10-09]. （原始内容于2006-05-19）. (open access publication)
^Bert. Fraser- Reid; Bruno. Radatus. 4,6-Di-O-acetyl-aldehydo-2,3-dideoxy-D-erythro-trans-hex-2-enose. Probable reason for the 'al' in Emil Fischer's triacetyl glucal. J. Am. Chem. Soc. 1970, 92: 5288–5290. doi:10.1021/ja00720a087.
^Eleuterio Alvarez; Maria T. Diaz; Ricardo Perez; Jose L. Ravelo; Alicia Regueiro; Jose A. Vera; Dacil Zurita; Julio D. Martin. Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations. J. Org. Chem. 1994, 59: 2848. doi:10.1021/jo00089a034.
^Ferrier, R. J. Unsaturated carbohydrates. Part IX. Synthesis of 2,3-dideoxy-α-D-erythro-hex-2-enopyranosides from tri-O-acetyl-D-glucal. Journal of the Chemical Society C Organic. 1969: 570. doi:10.1039/J39690000570.
^Ferrier, R. J. Unsaturated carbohydrates. Part X. Epoxidations and hydroxylations of 2,3-dideoxy-α-D-hex-2-enopyranosides. The four methyl 4,6-di-O-acetyl-2,3-anhydro-α-D-hexopyranosides. Journal of the Chemical Society C Organic. 1969: 575. doi:10.1039/J39690000575.
^Kelly, David R. Catalytic tin radical mediated tricyclisations. Part 1. Monocyclisation studies. Journal of the Chemical Society Perkin Transactions 1. 2000: 1559. doi:10.1039/b000661k.
^Kelly, David R. Catalytic tin radical mediated tricyclisations. Part 2. Journal of the Chemical Society Perkin Transactions 1. 2000: 1571. doi:10.1039/b000662i.
^Donohoe, Timothy J. Synthesis of amino-sugars using the directed dihydroxylation reaction. Chemical Communications. 1999: 1733. doi:10.1039/a904991f.
^ Kozikowski, AP, Pyeong-uk Park. Synthesis of 2-substituted δ3-piperidines: the nitrogen analog of the Ferrier rearrangement. An approach to streptazolin. J. Org. Chem. 1984, 49 (9): 1674–1676. doi:10.1021/jo00183a044.
十二月 27, 2023
费里尔重排反应, 提示, 此条目的主题不是费里尔, 型重排反应, ferrier, rearrangement, 由糖化学家罗伯特, 费里尔, robert, ferrier, 首先报道, 烯糖, 不饱和糖苷, 经亲核取代反应, 生成烯丙基重排的产物, 典型的费里尔重排目录, 反应机理, 例子, 改进法, 生成c, 糖苷, 含氮底物, 参见, 参考资料反应机理, 编辑首先在路易斯酸, 如氯化铟或三氟化硼, 作用下, 乙酸根离子离去, 产生离域的氧杂烯丙基碳正离子, 接下来, 原位与醇作用, 生成2, 糖苷的α, 和. 提示 此条目的主题不是费里尔 型重排反应 费里尔重排反应 Ferrier rearrangement 由糖化学家罗伯特 费里尔 Robert J Ferrier 首先报道 1 烯糖 2 3 不饱和糖苷 经亲核取代反应 生成烯丙基重排的产物 典型的费里尔重排目录 1 反应机理 2 例子 3 改进法 3 1 生成C 糖苷 3 2 含氮底物 4 参见 5 参考资料反应机理 编辑首先在路易斯酸 如氯化铟或三氟化硼 作用下 乙酸根离子离去 产生离域的氧杂烯丙基碳正离子 2 接下来 2 原位与醇作用 生成2 糖苷的a 3 和b 4 异头物 同时双键迁移至3 4 位 2 例子 编辑路易斯酸 醇 条件 结果InCl3 甲醇 二氯甲烷溶剂 a b 7 1 3 二噁烷 水 加热 75 产率 4 SnCl4 甲醇 二氯甲烷溶剂 78 10分钟 83 产率 a b 86 14 5 BF3 O C2H5 2 异丙醇 二氯甲烷溶剂 室温 24小时 95 产率 6 7 ZnCl2 乙醇 甲苯溶剂 室温 30 60分钟 65 95 产率 a b 89 11 8 9 BF3 O C2H5 2 苄醇 二氯甲烷溶剂 20 至室温 1小时 98 产率 10 改进法 编辑生成C 糖苷 编辑 用硅烷替代醇 可得C 糖苷 如果硅烷为三乙基硅烷 R H 则反应后得到3 4 不饱和脱氧糖 2 nbsp 利用费里尔重排生成C 糖苷含氮底物 编辑 1984年 Kozikowski 等报道了氮杂的费里尔重排 用于抗生素 streptazolin 的合成 11 nbsp 氮杂费里尔重排参见 编辑化学反应列表参考资料 编辑 Ferrier Robert J Unsaturated Carbohydrates Part 21 A Carboxylic Ring Closure of a Hex 5 enopyranoside Derivative J Chem Soc Perkin Trans 1 1979 1455 1458 doi 10 1039 P19790001455 2 0 2 1 Konstantinovic Stanimir et al The Ferrier rearrangement as the key step in the synthesis of C7 C16 alkyl 2 3 dideoxy glucosides from glucose and C7 C16 alkanols PDF J Serb Chem Soc 2001 66 8 499 505 2009 10 09 原始内容存档 PDF 于2011 10 08 Boga S B Balasubramanian K K Indium trichloride catalyzed Ferrier rearrangement facile synthesis of 2 3 unsaturated glycosides Arkivoc 2004 87 102 2009 10 09 原始内容存档于2006 05 19 open access publication Bert Fraser Reid Bruno Radatus 4 6 Di O acetyl aldehydo 2 3 dideoxy D erythro trans hex 2 enose Probable reason for the al in Emil Fischer s triacetyl glucal J Am Chem Soc 1970 92 5288 5290 doi 10 1021 ja00720a087 Eleuterio Alvarez Maria T Diaz Ricardo Perez Jose L Ravelo Alicia Regueiro Jose A Vera Dacil Zurita Julio D Martin Simple Designs for the Construction of Complex trans Fused Polyether Toxin Frameworks A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon Carbon or Carbon Oxygen Bond Forming Cyclizations J Org Chem 1994 59 2848 doi 10 1021 jo00089a034 Ferrier R J Unsaturated carbohydrates Part IX Synthesis of 2 3 dideoxy a D erythro hex 2 enopyranosides from tri O acetyl D glucal Journal of the Chemical Society C Organic 1969 570 doi 10 1039 J39690000570 Ferrier R J Unsaturated carbohydrates Part X Epoxidations and hydroxylations of 2 3 dideoxy a D hex 2 enopyranosides The four methyl 4 6 di O acetyl 2 3 anhydro a D hexopyranosides Journal of the Chemical Society C Organic 1969 575 doi 10 1039 J39690000575 Kelly David R Catalytic tin radical mediated tricyclisations Part 1 Monocyclisation studies Journal of the Chemical Society Perkin Transactions 1 2000 1559 doi 10 1039 b000661k Kelly David R Catalytic tin radical mediated tricyclisations Part 2 Journal of the Chemical Society Perkin Transactions 1 2000 1571 doi 10 1039 b000662i Donohoe Timothy J Synthesis of amino sugars using the directed dihydroxylation reaction Chemical Communications 1999 1733 doi 10 1039 a904991f Kozikowski AP Pyeong uk Park Synthesis of 2 substituted d3 piperidines the nitrogen analog of the Ferrier rearrangement An approach to streptazolin J Org Chem 1984 49 9 1674 1676 doi 10 1021 jo00183a044 取自 https zh wikipedia org w index php title 费里尔重排反应 amp oldid 79719481, 维基百科，wiki，书籍，书籍，图书馆，
