(2S,3S,4R,5S)-2-methylpiperidine-3,4,5-triol | 135395-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,3S,4R,5S)-2-methylpiperidine-3,4,5-triol
• 英文别名: 1,6-dideoxy-L-altronojirimycin；5-amino-1,5,6-trideoxyaltrose；L-1,6-dideoxyaltrojirimycin
• CAS: 135395-60-7
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: VYOCYWDJTQRZLC-OMMKOOBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(3R,4R,5S)-6-azido-3,4,5-trihydroxy-2-oxohexyl] dihydrogen phosphate 以45%的产率得到
  参考文献：
  名称：

  KAJIMOTO, TETSUYA;CHEN, LIHREN;LIU, KEVIN K. -C.;WONG, CHI-HUEY, J. AMER. CHEM. SOC., 113,(1991) N7, C. 6678-6680

  摘要：

  DOI：

文献信息

• Chelate-Controlled Asymmetric Synthesis of 2-Substituted 2,3-Dihydropyridin-4(1H)-ones: Synthesis ofD- andL-aminodeoxyaltrose derivatives
  作者：Jacques Streith、Arnaud Boiron、Jean-Louis Paillaud、Elsa-Maria Rodriguez-Perez、Christiane Strehler、Th�ophile Tschamber、Margareta Zehnder

  DOI：10.1002/hlca.19950780106

  日期：1995.2.8

  Asymmetric methylation and phenylation of the chiral pyridinium salt 7, as well as methylation of chiral pyridinium salt 18, with Grignard reagents occurred in good yield and with good-to-excellent diastereoselectivities (Schemes 2 and 3, resp.). These results are best explained by assuming chelate control to govern the asymmetric alkylation/arylation process. The minimum-energy conformations of the

  不对称甲基化和手性的吡啶鎓盐的苯基化7，以及手性的吡啶鎓盐的甲基化18，与格氏试剂发生在良好的产率和具有良好至优秀非对映选择性（方案2和3，RESP）。通过假定螯合剂控制非对称烷基化/芳基化过程，可以最好地解释这些结果。由“分子模拟Cerius-Dreiding II”程序确定的面外扭曲吡啶鎓盐7和18的最小能量构象与假定的不对称螯合物控制机制高度吻合。
• New Building Block for Polyhydroxylated Piperidine:  Total Synthesis of 1,6-Dideoxynojirimycin
  作者：Rajesh Rengasamy、Marcus J. Curtis-Long、Woo Duck Seo、Seong Hun Jeong、Ill-Yun Jeong、Ki Hun Park

  DOI：10.1021/jo702480y

  日期：2008.4.1

  (3R,4S)-3-Hydroxy-4-N-allyl-N-Boc-amino-1-pentene 10, an important precursor for the synthesis of polyhydroxylated piperidines, has been achieved as a single diastereomer without racemization via vinyl Grignard addition to N-Boc-N-allyl aminoaldehyde 9, which was derived from an enantiopure natural amino acid. Having forged a tetrahydropyridine ring scaffold 13 from 10 in 85% yield via RCM using Grubbs II catalyst, we were able to effect its stereo-divergent dihydroxylation, via a common epoxide intermediate to yield a range of interesting hydroxylated piperidines, including ent-1,6-dideoxynojirimycin (ent-1,6-dDNJ) 1 (28% overall yield) and 5-amino-1,5,6-trideoxyaltrose 2 (29% over all yield) in excellent dr. To the best of our knowledge, our synthesis of ent-1,6-dDNJ 1 is the most expeditious to date.

  (3R,4S)-3-羟基-4-N-烯丙基-N-Boc-氨基-1-戊烯 10 是一种重要的聚羟基哌啶类化合物合成前体， 通过乙烯格氏加成反应由对映纯天然氨基酸衍生的 N-Boc-N-烯丙基氨基乙醛 9 制得， 成品为单一双相异构体且无消旋化现象。采用格拉布催化剂II 进行环化复分解反应（RCM）， 由10 得到四氢吡啶环骨架13， 收率85%。随后， 经过相同环氧中间体， 我们实现了四氢吡啶环骨架13的立体发散性双羟基化， 得到一系列有趣的羟基化哌啶类化合物， 包括ent-1,6-去氧诺吉霉素（ent-1,6-dDNJ）1 和5-氨基-1,5,6-三去氧赤霉糖 2， 其中ent-1,6-dDNJ的总体收率为28%，5-氨基-1,5,6-三去氧赤霉糖的收率为29%， 均具有优秀的非对映异构体比率。据我们所知， 我们的ent-1,6-dDNJ合成路线是到目前为止最为高效的。
• A General Synthesis of Iminosugars
  作者：Ciaran McDonnell、Linda Cronin、Julie L. O'Brie、Paul V. Murphy

  DOI：10.1021/jo035763u

  日期：2004.5.1

  1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyI azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.
• Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars
  作者：Kevin K. C. Liu、Tetsuya Kajimoto、Lihren Chen、Ziyang Zhong、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/jo00022a013

  日期：1991.10

  The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described. Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized. Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-omega-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose. Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose. Explanations for the stereoselectivity in the hydrogenolysis reactions were provided. Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases. A new empirical formula is developed to relate the inhibition constants and inhibitor binding for alpha- and beta-glucosidases.
• Kajimoto, Tetsuya; Chen, Lihren; Liu, Kevin K.-C., Journal of the American Chemical Society, 1991, vol. 113, # 18, p. 6678 - 6680
  作者：Kajimoto, Tetsuya、Chen, Lihren、Liu, Kevin K.-C.、Wong, Chi-Huey

  DOI：——

  日期：——