tert-butyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 158742-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: tert-butyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,3S,6R)-2-(hydroxymethyl)-6-[(2-methylpropan-2-yl)oxy]-3,6-dihydro-2H-pyran-3-ol
• CAS: 158742-25-7
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: OCLFLMKRIVWVNW-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 咪唑 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 ((2R,3S,6R)-3-Allyloxy-6-tert-butoxy-3,6-dihydro-2H-pyran-2-yl)-methanol
  参考文献：
  名称：

  Palladium-catalysed cyclisation of chiral carbohydrate-derived geminal diacetates

  摘要：

  The Pd(0) and Pd(II)-catalysed cyclisation/functionalisation reactions of acyclic carbohydrate-derived 1,1-diacetoxy-2,7-diene and 1,1-diacetoxy-2-en-7-yne compounds proceeded in a stereospecific fashion to furnish chiral, multi-functionalised furanoid and cyclopentanoid products. The products contained valuable enolacetate moieties. which can be further elaborated to enable the facile entry to an array of substituted five membered ring compounds. (C) 1999 Elsevier Science Ltd. AIL rights reserved.

  DOI：

  10.1016/s0040-4020(98)01155-7
• 作为产物：
  描述：

  tert-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以99%的产率得到tert-butyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Palladium-catalysed cyclisation of chiral carbohydrate-derived geminal diacetates

  摘要：

  The Pd(0) and Pd(II)-catalysed cyclisation/functionalisation reactions of acyclic carbohydrate-derived 1,1-diacetoxy-2,7-diene and 1,1-diacetoxy-2-en-7-yne compounds proceeded in a stereospecific fashion to furnish chiral, multi-functionalised furanoid and cyclopentanoid products. The products contained valuable enolacetate moieties. which can be further elaborated to enable the facile entry to an array of substituted five membered ring compounds. (C) 1999 Elsevier Science Ltd. AIL rights reserved.

  DOI：

  10.1016/s0040-4020(98)01155-7

文献信息

• 2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies
  作者：Mohammad Saquib、Irfan Husain、Smriti Sharma、Garima Yadav、Vipul K. Singh、Sandeep K. Sharma、Priyanka Shah、Mohammad Imran Siddiqi、Brijesh Kumar、Jawahar Lal、Girish K. Jain、Brahm S. Srivastava、Ranjana Srivastava、Arun K. Shaw

  DOI：10.1016/j.ejmech.2011.03.002

  日期：2011.6

  The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents. These easily accessible, small molecules were found to exhibit in vitro activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.78 mu g/mL to 25 mu g/mL. A detailed SAR study on these hex-2-enopyranosid-4-uloses led to the identification of compound 5g (5007-724) which on the basis of low MIC (0.78 mu g/mL-M. tuberculosis H37Rv; 1.56 mu g/mL-MDR, SDR strains of M. tuberculosis; 0.78 mu g/mL-inhibition of intracellular replication of M. tuberculosis) and SI value of 13.5 has been identified as a promising lead molecule. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Liang, David Woei-Ming; Lin, Shu-Fu; Yap, Wen-Yen, Journal of the Chinese Chemical Society, 1994, vol. 41, # 2, p. 175 - 180
  作者：Liang, David Woei-Ming、Lin, Shu-Fu、Yap, Wen-Yen、Deng, Yea-Wen

  DOI：——

  日期：——
• Palladium-Mediated Cyclization on Carbohydrate Templates. 1. Synthesis of Enantiopure Bicyclic Compounds
  作者：Jean-Flaubert Nguefack、Véronique Bolitt、Denis Sinou

  DOI：10.1021/jo961881o

  日期：1997.3.1

  The bromo unsaturated carbohydrates 30 and 9 were prepared from ethyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside (1a) and (7) by deacetylation followed by monosilylation with TBDMSCl and then alkylation with BrCH2CBr=CH2. The three analogues 6 and 10 were obtained using the same methodology after inversion at C-4 via a Mitsunobu reaction. The N- and C-analogues 4b and 5 were prepared by palladium alkylation of the carbonate 2d with TsNHCH(2)CBr=CH2 and (CO(2)Me)(2)CHCH2CBr=CH2, respectively. Treatment of the unsaturated carbohydrates 3a and 9 with a catalytic amount of Pd(OAc)(2)/PPh(3) in CH3CN/H2O in the presence of Bu(4)NHSO(4) and NEt(3) afforded the bicyclic compound 14a. The N- and C-analogues 14b and 14c were obtained using the same conditions and starting, respectively, from 4b and 5. On the other hand, treatment of the three derivatives 6 and 10 under these conditions gave the furanic structure 15. In the case of compound 30, performing the reaction in the presence of sodium formate yielded the bicyclic 2-deoxy carbohydrate 17.