3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl bromide | 64605-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl bromide
• 英文别名: [(2S,3R,4S,6S)-3-acetyloxy-6-bromo-2-methyloxan-4-yl] acetate
• CAS: 64605-20-5
• 化学式: C₁₀H₁₅BrO₅
• 分子量: 295.13
• InChiKey: DCYXHMVVTCMQQC-UKIQFFJBSA-N

物化性质

• 沸点：
  315.0±42.0 °C(predicted)
• 密度：
  1.44±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl bromide 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 二甲基二环氧乙烷 作用下， 以 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 24.0h， 生成 methyl 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl-(1->4)-2,3,6-trideoxy-3-C-methyl-3-nitro-β-L-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  Glycosylation of Branched Amino and Nitro Sugars. 2. Synthesis of the Cororubicin Trisaccharide

  摘要：

  The synthesis of the nitro-sugar-containing trisaccharide found in the antibiotic cororubicin is described. This trisaccharide contains the nitro sugar L-decilonitrose which is attached to two digitoxose residues (a dideoxy sugar) by beta-1,4 and alpha-1,4 linkages. The target trisaccharide synthesized was methyl 2,6-dideoxy-alpha-L-lyxo-hexopyranosyl-(1-->4)-2,3,6-trideoxy-3-C-methyl-3-nitro-beta-L-ribo-hexopyranosyl-( 1-->4)-2,6-dideoxy-alpha-L-lyxo-hexopyranoside The principle features of the synthesis are the use of an O-benzylhydroxylamino sugar as the precursor to the nitro sugar decilonitrose and as both the acceptor and donor in glycosyations, a beta-selective glycosylation by means of a thioglycoside donor, and novel functional group transformations carried out on the assembled trisaccharide. These include oxidative cleavage of the O-benzylhydroxylamino group to nitro, carried out with dimethyldioxirane in one step. This transformation proved critical in completing the synthesis, which is the first reported of one of the decilonitrose-containing trisaccharides found in antibiotics.

  DOI：

  10.1021/jo990403l
• 作为产物：
  描述：

  2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl bromide
  参考文献：
  名称：

  [EN] NOVEL SUGAR DERIVATIVES AND USES THEREOF TO PREPARE NOVEL SENOLYTIC AGENTS
  [FR] NOUVEAUX DÉRIVÉS DE SUCRE ET LEURS UTILISATIONS POUR PRÉPARER DE NOUVEAUX AGENTS SÉNOLYTIQUES

  摘要：

  Provided herein are novel sugar derivatives which are intermediates for preparing senolytic agents that selectively kill senescent cells associated with numerous pathologies and diseases, including age-related pathologies and diseases.

  公开号：

  WO2023039292A2

文献信息

• Cromer, Remy; Spohr, Ulrike; Khare, Deveshwari P., Canadian Journal of Chemistry, 1992, vol. 70, # 5, p. 1511 - 1530
  作者：Cromer, Remy、Spohr, Ulrike、Khare, Deveshwari P.、LePendu, Jacques、Lemieux, Raymond U.

  DOI：——

  日期：——
• FLORENT, J. C.;GENOT, A.;MONNERET, C., J. ANTIBIOTICS , 42,(1989) N2, C. 1823-1830
  作者：FLORENT, J. C.、GENOT, A.、MONNERET, C.

  DOI：——

  日期：——
• GENOT, AGNES;FLORENT, JEAN-CLAUDE;MONNERET, CLAUDE, J. CARBOHYDR. CHEM., 10,(1991) N, C. 91-95
  作者：GENOT, AGNES、FLORENT, JEAN-CLAUDE、MONNERET, CLAUDE

  DOI：——

  日期：——
• US4302449A
  申请人：——

  公开号：US4302449A

  公开（公告）日：1981-11-24
• [EN] COUMARIN DERIVATIVES OF SUGAR ANALOGS AND USES THEREOF<br/>[FR] DÉRIVÉS DE COUMARINE D'ANALOGUES DE SUCRE ET LEURS UTILISATIONS
  申请人：[en]RUBEDO LIFE SCIENCES, INC.

  公开号：WO2023039293A1

  公开（公告）日：2023-03-16

  Provided herein are coumarin derivatives of sugar analogs which are used to measure the rate of hydrolysis of these sugar analogs when contacted with a glycosidase. The reactivity of the coumarin derivatives serves as a convenient method for estimating for the rate of hydrolysis of sugar analogs when used a promoiety with cytotoxic drugs to generate senolytic agents with improved selectivity for killing senescent cells.