(2S,3R,4S)-N-tert-butyloxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidene-proline | 117781-10-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,4S)-N-tert-butyloxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidene-proline
• 英文别名: (2S,3R,4S)-N-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxyproline；(2R,3R,4S)-N-tert-butoxycarbonyl-3,4-dihydroxyproline isopropylidene acetal；(2R,3R,4S)-N-(tert-butoxycarbonyl)-3,4-isopropylidenedioxyproline；(3AR,4S,6AS)-5-(Tert-butoxycarbonyl)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-C]pyrrole-4-carboxylic acid；(3aR,4S,6aS)-2,2-dimethyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid
• CAS: 117781-10-9
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: FRDGVQODRPFOOR-CIUDSAMLSA-N

物化性质

• 沸点：
  407.8±45.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-N-tert-butyloxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidene-proline 在 二异丁基氢化铝 、 三氟乙酸 作用下， 以 乙醚 、 正己烷 、 水 为溶剂， 反应 24.25h， 生成 (2R,3R,4S)-2-(羟基甲基)吡咯烷-3,4-二醇
  参考文献：
  名称：

  Asymmetric synthesis of 1,4-dideoxy-1,4-imino-d-ribitol via stereoselective addition of allylphenylsulfone to an aryl N-sulfinylimine

  摘要：

  Asymmetric synthesis of 1,4-dideoxy-1,4-imino-D-ribitol was achieved utilizing the stereoselective addition of allylphenylsulfone to a chiral N-suffinyl-2-furfuryl imine and ring-closing metathesis reactions as key steps. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00033-2
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-D-gulitol 在 4-二甲氨基吡啶 、 palladium on activated charcoal sodium chlorite 、 sodium periodate 、 potassium dihydrogenphosphate 、 氢气 、 溶剂黄146 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 114.67h， 生成 (2S,3R,4S)-N-tert-butyloxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidene-proline
  参考文献：
  名称：

  Polyhydroxylated pyrrolidines from sugar lactomes: Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol from d-galactonolactone and syntheses of 1,4-dideoxy-1,4-imino-d-allitol, 1,4-dideoxy-1,4-imino-d-ribitol, and (2s,3r,4s)-3,4-dihydroxyproline from d-gulonolactone

  摘要：

  DOI：

  10.1016/s0040-4020(01)81716-6

文献信息

• Ring-Closing Metathesis of Chiral Allylamines. Enantioselective Synthesis of (2<i>S</i>,3<i>R</i>,4<i>S</i>)-3,4-Dihydroxyproline
  作者：Rubén Martín、Montserrat Alcón、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/jo025832p

  日期：2002.10.1

  The ring-closing metathesis (RCM) of two types of unsaturated chiral allylamines III, easily available from enantiomerically enriched epoxy alcohols, has been studied. Fully protected allylamines IIIa [(1)R = CH(2)-(CH(2))(n)()-CH=CH(2); (2)R = Boc; (3)R = PMB] have been prepared from unsaturated epoxy alcohols, whereas bis-allylamines IIIb ((1)R = Ph, (2)R = allyl,(3)R = Boc or PMB) have been prepared

  研究了两种容易从对映异构体富集的环氧醇中获得的不饱和手性烯丙胺III的闭环易位（RCM）。完全保护的烯丙胺IIIa [（1）R = CH（2）-（CH（2））（n）（）-CH = CH（2）; （2）R = Boc; （3）R = PMB]由不饱和环氧醇制备，而双烯丙基胺IIIb（（1）R = Ph，（2）R =烯丙基，（3）R = Boc或PMB）已由2， 3-环氧-3-苯基丙醇。两种类型均已进行了RCM处理，以提供环状烯丙胺I或II。这些中间体的合成潜力已通过（2S，3R，4S）-3,4-二羟基脯氨酸的对映选择性合成得到证明。
• Stereoselective Synthesis of (+)-1,8-Di-epi- and (-)-1-epi-Swainsonine from an (S)-Pyroglutamic Acid Derivative.
  作者：Nobuo IKOTA

  DOI：10.1248/cpb.41.1717

  日期：——

  (+)-1, 8-Di-epi-swainsonine (15) and (-)-1-epi-swainsonine (17) were synthesized stereoselectively from an (S)-pyroglutamic acid derivative (1a). A (2R, 3R, 4R)-3, 4-dihydroxy-2-hydroxymethylpyrrolidine derivative (6a) was prepared by cis-dihydroxylation of an α, β-unsaturated lactam (2) followed by epimerization of the di-O-benzyl derivative (3b) as the key reactions. The diastereoselective allylation of the aldehyde 6b obtained from 6a and subsequent cyclization of 13 and 16 gave 15 and 17, respectively. It proved that 1, 8-di-epi-swainsonine (15) is dextrorotatory.

  由(S)-焦谷氨酸衍生物(1a)立体选择性合成(+)-1, 8-二-表-苦马豆素(15)和(-)-1-表-苦马豆素(17)。 (2R, 3R, 4R)-3, 4-二羟基-2-羟甲基吡咯烷衍生物 (6a) 通过 α, β-不饱和内酰胺 (2) 的顺式二羟基化和二-O-苄基衍生物的差向异构化制备(3b)为关键反应。由6a获得的醛6b的非对映选择性烯丙基化以及随后13和16的环化分别得到15和17。证明1, 8-二-表-苦豆素(15)具有右旋性。
• Total synthesis of both enantiomers of trans-2,3-cis-3,4-dihydroxyproline
  作者：Franca Zanardi、Lucia Battistini、Marika Nespi、Gloria Rassu、Pietro Spanu、Mara Cornia、Giovanni Casiraghi

  DOI：10.1016/0957-4166(96)00123-1

  日期：1996.4

  Both enantiomers of trans-2,3-cis-3,4-dihydroxyproline, 4 and 5, have been stereoselectively synthesized from 2,3-O-isopropylidene-D-glyceraldehyde 1, by taking advantage of a divergent and parallel synthetic strategy, utilizing N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as the common four-carbon synthon. Copyright (C) 1996 Elsevier Science Ltd
• Stereospecific Cyclization Strategies for α,ε-Dihydroxy-β-amino Esters: Asymmetric Syntheses of Imino and Amino Sugars
  作者：Stephen G. Davies、Emma M. Foster、James A. Lee、Paul M. Roberts、James E. Thomson

  DOI：10.1021/jo5018298

  日期：2014.10.17

  A range of biologically significant imino and amino sugars [1,4-dideoxy-1,4-imino-D-allitol, 3,6-dideoxy-3,6-imino-L-allonic acid, (3R,4S)-3,4-dihydroxy-L-proline, 1,5-anhydro-4-deoxy-4-amino-D-glucitol, and 1,5-anhydro-4-deoxy-4-amino-L-iditol] has been prepared via stereospecific cyclization of alpha,epsilon-dihydroxy-beta-amino esters. These substrates are readily prepared via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure alpha,beta-unsaturated esters (beta-substituted with cis- and trans-dioxolane units) coupled with in situ enolate oxidation with camphorsulfonyloxaziridine (CSO). Activation of the epsilon-hydroxyl group allowed cyclization to either the corresponding pyrrolidine or the tetrahydropyran scaffold, with the course of the cyclization process being dictated by the relative configuration of the dioxolane unit. When the alpha,epsilon-dihydroxy-beta-amino ester bears a cis-dioxolane unit, cyclization occurs upon attack of the beta-amino substituent to give the corresponding pyrrolidine after in situ N-debenzylation. In contrast, when the alpha,epsilon-dihydroxy-beta-amino ester bears a trans-dioxolane unit, cyclization occurs upon attack of the alpha-hydroxyl substituent to give the corresponding tetrahydropyran.
• FLEET, GEORGE W. J.;SON, JONG CHAN, TETRAHEDRON, 44,(1988) N 9, C. 2637-2647
  作者：FLEET, GEORGE W. J.、SON, JONG CHAN

  DOI：——

  日期：——