3,6-(tert-butoxycarbonyl)imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose | 294172-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3,6-(tert-butoxycarbonyl)imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose
• 英文别名: tert-butyl (3aR,4S,6aS)-2,2-dimethyl-4-(2-oxoethyl)-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 294172-61-5
• 化学式: C₁₄H₂₃NO₅
• 分子量: 285.34
• InChiKey: KFLLNOAAZZZKLG-GARJFASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-(tert-butoxycarbonyl)imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose 在 palladium dihydroxide lithium aluminium tetrahydride 、 正丁基锂 、 氢气 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 21.25h， 生成 (Z)-1,6-anhydro-3-{3',6'-[(tert-butoxy)carbonyl]imino-1',2',3',6'-tetradeoxy-4',5'-O-isopropylidene-L-arabino-hexitol-1'-C-ylidene}-3-deoxy-β-D-xylo-hexopyranose
  参考文献：
  名称：

  Synthesis of (Z)-3-Deoxy-3-(1,2,3,6-Tetradeoxy-3,6-Imino-L-Arabino-Hexitol-1-C-Ylidene)-D-Xylo-Hexose Derivatives. First Examples Of Homo-(1→3)-C-Linked Iminodisaccharides.

  摘要：

  Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).

  DOI：

  10.1080/07328300008544099
• 作为产物：
  描述：

  ethyl 3,6-[(benzyloxy)carbonyl]imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexonate 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 3,6-(tert-butoxycarbonyl)imino-2,3,6-trideoxy-4,5-O-isopropylidene-L-arabino-hexose
  参考文献：
  名称：

  Synthesis of (Z)-3-Deoxy-3-(1,2,3,6-Tetradeoxy-3,6-Imino-L-Arabino-Hexitol-1-C-Ylidene)-D-Xylo-Hexose Derivatives. First Examples Of Homo-(1→3)-C-Linked Iminodisaccharides.

  摘要：

  Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).

  DOI：

  10.1080/07328300008544099

文献信息

• Synthesis and glycosidase inhibitory activities of 2-(aminoalkyl)pyrrolidine-3,4-diol derivatives
  作者：Ana T Carmona、Florence Popowycz、Sandrine Gerber-Lemaire、Eliazar Rodrı́guez-Garcı́a、Catherine Schütz、Pierre Vogel、Inmaculada Robina

  DOI：10.1016/j.bmc.2003.09.020

  日期：2003.11

  Several 2-(aminomethyl)-and 2-(2-aminoethyl)-pyrrolidine-3,4-diol derivatives have been assayed for their inhibitory activities towards glycosidases. Good inhibitors of alpha-mannosidases must have the (2R,3R,4S) configuration and possess 2-(benzylamino)methyl substituents. Stereomers with the (2S,3R,4S) configuration are also competitive inhibitors of alpha-mannosidases, but less potent as they share

  已经测定了几种2-（氨基甲基）-和2-（2-氨基乙基）-吡咯烷-3，4-二醇衍生物对糖苷酶的抑制活性。好的α-甘露糖苷酶抑制剂必须具有（2R，3R，4S）构型并具有2-（苄基氨基）甲基取代基。具有（2S，3R，4S）构型的立体异构体也是α-甘露糖苷酶的竞争性抑制剂，但效力较低，因为它们共享β-D-甘露糖苷的C（1），C（2），C（3）构型比α-D-甘露糖苷 有趣的是，（2S，3R，4S）-2- [2-[（（4-苯基）苯基氨基]乙基]吡咯烷-3,4-二醇（12g）抑制几种酶，例如牛附睾中的α-L-岩藻糖苷酶（ K（i）= 6.5microM，竞争性），来自牛肝的α-半乳糖苷酶（K（i）= 5microM，混合）和来自杰克豆的α-半乳糖苷酶（K（i）= 102microM，混合）。二胺，例如（2R，3S，
• A convenient stereoselective route to novel tetrahydroxyindolizidines
  作者：Ana T. Carmona、José Fuentes、Inmaculada Robina

  DOI：10.1016/s0040-4039(02)02084-1

  日期：2002.11

  A convenient stereoselective route, for the preparation of novel tetrahydroxyindolizidines, based on syn-hydroxylation reactions of alkenyl pyrrolidines followed by cyclization, is reported. Derivatives of (+)-swainsonine are prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Carmona, Ana T.; Fuentes, Jose; Robina, Inmaculada, Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3874 - 3883
  作者：Carmona, Ana T.、Fuentes, Jose、Robina, Inmaculada、Garcia, Eliazar Rodriguez、Demange, Raynald、Vogel, Pierre、Winters, Ana L.

  DOI：——

  日期：——
• Synthesis of Pyrrolidine 3,4-Diol Derivatives with Anticancer Activity on Pancreatic Tumor Cells
  作者：Inmaculada Robina、Frederic Steimer、Ana T. Carmona、Antonio J. Moreno-Vargas、Irene Caffa、Fabrizio Montecucco、Alessio Nencioni、Pierre Vogel

  DOI：10.3987/com-13-s(s)111

  日期：——

  Novel pyrrolidine 3,4-diol derivatives of the type (2R and 2S,3R,45)[(( 1R)-1-methoxycarbonyl and hydroxylmethyl)-1-arylmethyl)amino] ethyl}-pyrrolidine-3,4-diol have been prepared and evaluated as a-mannosidase inhibitors and assayed for their anticancer activity in vitro. They all exhibit specific but moderate activity as inhibitors towards a-mannosidase from Jack beans. Compounds 7 and 8b bearing hydroxymethyl and trifluoromethylbiphenyl groups show the best antiproliferative effect in two pancreatic cancer cell lines.
• Synthesis of (<i>Z</i>)-3-Deoxy-3-(1,2,3,6-Tetradeoxy-3,6-Imino-L-<i>Arabino</i>-Hexitol-1-<i>C</i>-Ylidene)-D-<i>Xylo</i>-Hexose Derivatives. First Examples Of Homo-(1→3)-<i>C</i>-Linked Iminodisaccharides.
  作者：Francesca Cardona、Inmaculada Robina、Pierre Vogel

  DOI：10.1080/07328300008544099

  日期：2000.1

  Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).