2,3,6-tri-O-acetyl-4-deoxy-α-D-xylo-hexopyranosyl bromide | 28434-40-4

• 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: 2,3,6-tri-O-acetyl-4-deoxy-α-D-xylo-hexopyranosyl bromide
• 英文别名: [(2S,4S,5R,6R)-4,5-diacetyloxy-6-bromooxan-2-yl]methyl acetate
• CAS: 28434-40-4
• 化学式: C₁₂H₁₇BrO₇
• 分子量: 353.167
• InChiKey: QLZTUCXOUSRWSQ-YFKTTZPYSA-N

物化性质

• 沸点：
  385.7±42.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-acetyl-4-deoxy-α-D-xylo-hexopyranosyl bromide 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 四乙基溴化铵 、 sodium hydride 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-O-acetyl-3,6-di-O-benzyl-4-deoxy-α-D-xylo-hexopyranosyl bromide
  参考文献：
  名称：

  Lemieux, Raymond U.; Cromer, Remy; Spohr, Ulrike, Canadian Journal of Chemistry, 1988, vol. 66, p. 3083 - 3098

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-deoxy-D-xylo-hexopyranose 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以94 %的产率得到2,3,6-tri-O-acetyl-4-deoxy-α-D-xylo-hexopyranosyl bromide
  参考文献：
  名称：

  [EN] COUMARIN DERIVATIVES OF SUGAR ANALOGS AND USES THEREOF
  [FR] DÉRIVÉS DE COUMARINE D'ANALOGUES DE SUCRE ET LEURS UTILISATIONS

  摘要：

  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.

  公开号：

  WO2023039293A1

文献信息

• Recognition of β-d-Gal p-(1 → 3)-β-d-Glc pNAc-OR acceptor analogues by the Lewis α-(1 → 34)-fucosyltransferase from human milk
  作者：Minghui Du、Ole Hindsgaul

  DOI：10.1016/0008-6215(96)00047-x

  日期：1996.6

  The Lewis alpha-(1 --> 3/4)-frucosyltransferase (E.C. 2.4.1.65) transfers L-fucose from GDP-fucose to OH-4 of the Glc pNAc residue in the disaccharide beta-D-Gal p-(1 --> 3)-beta-D-Glc pNAc-OR [R = (CH2)(8)COOMe] (1) to give the Lewis-A blood group determinant beta-D-Gal p-(1 --> 3)-[alpha-L-Fuc p-(1 --> 4)]-beta-D-Glc pNAc-OR. Five deoxy analogues of 1, as well as its N-propionyl derivative, were chemically synthesized and kinetically evaluated as both substrates and inhibitors for the enzyme from human milk. The unmodified acceptor 1 had K-m = 640 mu M with V-max set arbitrarily to 100. The 6-deoxy (K-m = 400 mu M, V-max = 90) and N-propionyl compounds (K-m = 330 mu M, V-max = 170) remained excellent substrates while the 4-deoxy compound was a very weak competitive inhibitor with K-i = 9 mM. Deoxygenation of OH-2' and OH-4' (of the Gal residue) in 1 had little effect on the activity. The OH-6 group of the Gal residue proved to be critical for recognition by the enzyme since substitution of this group with hydrogen led to an inactive compound. (C) 1996 Elsevier Science Ltd.
• LEMIEUX, RAYMOND U.;CROMER, REMY;SPOHR, ULRIKE, CAN. J. CHEM., 66,(1988) N2, C. 3083-3098
  作者：LEMIEUX, RAYMOND U.、CROMER, REMY、SPOHR, ULRIKE

  DOI：——

  日期：——
• US4171356A
  申请人：——

  公开号：US4171356A

  公开（公告）日：1979-10-16
• [EN] DRUG CONJUGATES OF SUGAR DERIVATIVES AND USES THEREOF AS SENOLYTIC AGENTS<br/>[FR] CONJUGUÉS MÉDICAMENTEUX DE DÉRIVÉS DE SUCRE ET LEURS UTILISATIONS EN TANT QU'AGENTS SÉNOLYTIQUES
  申请人：[en]RUBEDO LIFE SCIENCES, INC.

  公开号：WO2023039600A1

  公开（公告）日：2023-03-16

  Provided herein are agents and methods for selectively killing senescent cells that are associated with numerous pathologies and diseases, including age-related pathologies and diseases. As disclosed herein, senescent cell-associated diseases and disorders may be treated or prevented by administering at least one senolytic agent or pharmaceutical compositions thereof. The senescent cell-associated diseases or disorders treated or prevented by the agents and methods described herein include, but are not limited to, cardiovascular diseases or disorders, cardiovascular diseases and disorders associated with arteriosclerosis, such as atherosclerosis, idiopathic pulmonary fibrosis (IPF), chronic obstructive pulmonary disease (COPD), osteoarthritis, inflammatory or autoimmune diseases or disorders, pulmonary diseases or disorders, neurological diseases or disorders, dermatological diseases or disorders, chemotherapeutic side effects, radiotherapy side effects, metastasis and metabolic diseases.