2,3-dideoxy-2-fluoro-L-glycero-tetronolactone | 86677-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2,3-dideoxy-2-fluoro-L-glycero-tetronolactone
• 英文别名: 2(S)-fluoro-γ-butyrolactone；2S-fluoro-4-butyrolactone；(3S)-3-fluorooxolan-2-one
• CAS: 86677-82-9
• 化学式: C₄H₅FO₂
• 分子量: 104.081
• InChiKey: QSGGLAGTJDEIAN-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dideoxy-2-fluoro-L-glycero-tetronolactone 生成 3(S)-fluoro-4-methyl-1,4-pentanediol
  参考文献：
  名称：

  SHIUEY, SHIAN-JAN;PARTRIDGE, JOHN J.;USKOKOVIC, MILAN R., J. ORG. CHEM., 53,(1988) N 5, 1040-1046

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(+)-α-羟基-γ-丁内酯 在 diethylaminosulfur trifluoride 作用下， 以 二氯甲烷 为溶剂， 生成 2,3-dideoxy-2-fluoro-L-glycero-tetronolactone
  参考文献：
  名称：

  Synthesis of 1.alpha.,25-dihydroxy-24R-fluorocholecalciferol and

  摘要：

  1.alpha.,25-二羟基-24R-氟胆钙化醇和1.alpha.,25-二羟基-24S-氟胆钙化醇是1.alpha.,25-二羟基胆钙化醇的类似物，是维生素D.sub.3生理上最活跃的代谢产物。这些新的类似物通过多步合成过程从已知物质1.alpha.,3.beta.-二羟基雄甾-5-烯-17-酮中合成。这些化合物具有增加肠道钙转运、增加血清钙和磷浓度以及增加这些矿物质在骨骼中沉积的能力。这些化合物将作为天然1.alpha.,25-二羟基胆钙化醇的替代品，在代谢性钙和磷缺乏的疾病状态的治疗中有广泛的应用。这些疾病状态的例子包括：骨硬化、抗癫痫治疗、骨质疏松症、成骨不全、继发性甲状旁腺功能亢进、甲状旁腺功能减退、甲状旁腺功能亢进、肝硬化、阻塞性黄疸、药物代谢、髓样癌、慢性肾脏疾病、低磷酸盐性VDRR、依赖维生素D的佝偻病、结节病、糖皮质激素拮抗、吸收不良综合征、脂肪泻、热带性肠道病和乳热。

  公开号：

  US04652405A1

文献信息

• Synthesis of 1.alpha.,25-dihydroxy-24R-fluorocholecalciferol and
  申请人：Hoffmann-La Roche Inc.

  公开号：US04634692A1

  公开（公告）日：1987-01-06

  1.alpha.,25-Dihydroxy-24R-fluorocholecalciferol and 1.alpha.,25-dihydroxy-24S-fluorocholecalciferol, analogs of 1.alpha.,25-dihydroxy-cholecalciferol which is physiologically the most active metabolite of vitamin D.sub.3, are synthesized in a multistep process from the known substance 1.alpha.,3.beta.-dihydroxyandrost-5-en-17-one. The new analogs are characterized by the ability to increase intestinal calcium transport, increase serum calcium and phosphate concentrations and to increase the deposition of these minerals in bones. These compounds will find a ready application as substitutes for natural 1.alpha.,25-dihydroxycholecalciferol in the treatment of disease states characterized by metabolic calcium and phosphate deficiencies. Exemplary of such disease states are the following: osteomalacia, osteoporosis, rickets, osteitis fibrosa cystica, renal osteodystrophy, osteosclerosis, anti-convulsant treatment, osteopenia, fibrogenesis-imperfecta ossium, secondary hyperparathyrodism, hypoparathyroidism, hyperparathyroidism, cirrhosis, obstructive jaundice, drug induced metabolism, medullary carcinoma, chronic renal disease, hypophosphatemic VDRR, vitamin D-dependent rickets, sarcoidosis, glucocorticoid antagonism, malabsorption syndrome, steatorrhea, tropical sprue, idiopathic hypercalcemia and milk fever.

  1.alpha.,25-二羟基-24R-氟胆钙化醇和1.alpha.,25-二羟基-24S-氟胆钙化醇是1.alpha.,25-二羟基胆钙化醇的类似物，它是维生素D.sub.3在生理上最活跃的代谢产物。这些新的类似物是通过从已知物质1.alpha.,3.beta.-二羟基雄烯-5-烯-17-酮进行多步合成的。这些新类似物的特点是能够增加肠道钙的转运，增加血清钙和磷浓度，并增加这些矿物质在骨骼中的沉积。这些化合物将作为天然1.alpha.,25-二羟基胆钙化醇的替代品，广泛应用于代谢性钙和磷缺乏的疾病状态的治疗中。这些疾病状态的例子包括：软骨病、骨质疏松症、佝偻病、纤维骨炎性囊性骨病、肾性骨病、骨硬化症、抗癫痫治疗、骨质疏松、纤维成骨不全、继发性甲状旁腺功能亢进症、甲状旁腺功能减退症、甲状旁腺功能亢进症、肝硬化、阻塞性黄疸、药物代谢、髓样癌、慢性肾病、低磷酸盐性VDRR、依赖维生素D的佝偻病、结节病、糖皮质激素拮抗、吸收不良综合征、脂肪泻、热带性肠道病和乳热等。
• Triply convergent synthesis of 1.alpha.,25-dihydroxy-24(R)-fluorocholecalciferol
  作者：Shian Jan Shiuey、John J. Partridge、Milan R. Uskokovic

  DOI：10.1021/jo00240a021

  日期：1988.3
• SHIUEY, SHIAN-JAN;PARTRIDGE, JOHN J.;USKOKOVIC, MILAN R., J. ORG. CHEM., 53,(1988) N 5, 1040-1046
  作者：SHIUEY, SHIAN-JAN、PARTRIDGE, JOHN J.、USKOKOVIC, MILAN R.

  DOI：——

  日期：——
• Syntheses of fluorinated ligands to probe binding of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, to antibodies
  作者：Alex H.C. Chang、Derek Horton、Pavol Kováč

  DOI：10.1016/s0957-4166(99)00505-4

  日期：2000.2

  Derivatives of methyl alpha-glycosides of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, specifically Fluorinated at position 2' or 4' have been synthesized by coupling the appropriately fluorinated derivatives of 3-deoxy-L-glycero-tetronic acid with the methyl oc-glycosides of perosamine. The compound having the fluorine atom at position 2 was obtained by electrophilic addition of fluorine to the glycal derived from the parent antigenic determinant, serotypes Inaba, using Selectfluor(TM) as a fluorination reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.