3-azido-3-deoxy-1:2,5:6-di-O-isopropylidene-α-D-gulofuranose | 244057-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azido-3-deoxy-1:2,5:6-di-O-isopropylidene-α-D-gulofuranose
• 英文别名: (3aR,5R,6R,6aR)-6-azido-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 244057-16-7
• 化学式: C₁₂H₁₉N₃O₅
• 分子量: 285.3
• InChiKey: UZVCUNUCGITLER-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-azido-3-deoxy-1:2,5:6-di-O-isopropylidene-α-D-gulofuranose 在 camphor-10-sulfonic acid 、 溴 、 barium carbonate 、 三氟乙酸 作用下， 反应 2.0h， 生成 (3R,4S,5R)-4-azido-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxyoxolan-2-one
  参考文献：
  名称：

  3-Azidotetrahydrofuran-2-carboxylates: monomers for five-ring templated β-amino acid foldamers?

  摘要：

  Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of beta-amino acid oligomers with secondary structure. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00205-0
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 在 吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 sodium azide 、 双氧水 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-azido-3-deoxy-1:2,5:6-di-O-isopropylidene-α-D-gulofuranose
  参考文献：
  名称：

  3-Azidotetrahydrofuran-2-carboxylates: monomers for five-ring templated β-amino acid foldamers?

  摘要：

  Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of beta-amino acid oligomers with secondary structure. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00205-0

文献信息

• Design, synthesis and the effect of 1,2,3-triazole sialylmimetic neoglycoconjugates on Trypanosoma cruzi and its cell surface trans-sialidase
  作者：Vanessa L. Campo、Renata Sesti-Costa、Zumira A. Carneiro、João S. Silva、Sergio Schenkman、Ivone Carvalho

  DOI：10.1016/j.bmc.2011.11.022

  日期：2012.1

  This work describes the synthesis of a series of sialylmimetic neoglycoconjugates represented by 1,4-disubstituted 1,2,3-triazole-sialic acid derivatives containing galactose modified at either C-1 or C-6 positions, glucose or gulose at C-3 position, and by the amino acid derivative 1,2,3-triazole fused threonine-3-O-galactose as potential TcTS inhibitors and anti-trypanosomal agents. This series was

  这项工作描述了一系列由1,4-二取代的1,2,3-三唑-唾液酸衍生物代表的一系列唾液酸模拟新糖缀合物的合成，这些衍生物包含在C-1或C-6位置修饰的半乳糖，在C-3处的葡萄糖或果糖位置，并由氨基酸衍生物1,2,3-三唑稠合的苏氨酸-3 - O-半乳糖作为潜在的TcTS抑制剂和抗锥蛋白药物。该系列是通过叠氮基官能化糖1-N 3 -Gal（商业），6-N 3 -Gal，3-N 3-的Cu（I）催化的叠氮化物-炔烃环加成反应（“点击化学”）获得的。 Glc和3-N 3 -Gul与相应的基于炔烃的2-丙炔基唾液酸，以及通过氨基酸N之间的点击化学反应具有3 - O-丙炔基-GalOMe的3 -ThrOBn。所述1,2,3-三唑连接的唾液酸-6- ö半乳糖和唾液酸吡喃半乳糖苷表现出较高的克氏锥虫 反-sialidase（TCTS）抑制活性为1.0毫米（约90％），而只有前者显示相关的杀锥虫活性（IC 50
• Cysteine Protease Inhibitors
  申请人：Tickle David

  公开号：US20090023747A1

  公开（公告）日：2009-01-22

  A compound of the formula (II) wherein one of R 1 and R 2 is halo and the other is H or halo; R 3 is —C 1 -C 5 straight or branched chain, optionally fluorinated, alkyl or —CH 2 CR 5 C 3 -C 4 -Cycloalkyl; R 4 is H; R 5 is H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, hydroxyl, OC 1 -C 2 alkyl, fluoro; R 6 is a stable, optionally substituted, monocyclic or bicyclic, carbocycle or heterocycle wherein the or each ring has 4, 5 or 6 ring atoms and 0 to 3 hetero atoms selected from S, O and N; Rb is haloalkyl; Rc is H or C 1 -C 4 alkyl; and pharmaceutically acceptable salts, hydrates or N-oxides thereof have utility in the treatment of disorders characterised by inappropriate expression or activation of cathepsin K, such as osteoporosis, osteoarthritis, rheumatoid arthritis or bone metastases.

  化合物的公式（II），其中R1和R2中的一个是卤素，另一个是氢或卤素; R3是直链或支链，可选择氟化的C1-C5烷基或-CH2CR5C3-C4环烷基; R4是氢; R5是氢，C1-C2烷基，C1-C2卤代烷基，羟基，OC1-C2烷基，氟; R6是稳定的，可选地取代的单环或双环，碳环或杂环，其中每个环具有4、5或6个环原子和0到3个从S、O和N中选择的杂原子; Rb是卤代烷基; Rc是氢或C1-C4烷基;以及其药学上可接受的盐，水合物或N-氧化物在治疗由于cathepsin K不适当的表达或激活而表现出来的疾病中具有用途，如骨质疏松症、骨关节炎、类风湿性关节炎或骨转移。
• Cysteine Protease inhibitors
  申请人：Nilsson Magnus

  公开号：US20080234260A1

  公开（公告）日：2008-09-25

  A compound of the formula II wherein one of R 1 and R 2 is halo and the other is H or halo; R 3 is C 1 -C 4 straight or branched chain, optionally fluorinated, alkyl; R 4 is H; or R 3 together with R 4 and the adjoining backbone carbon defines: a spiro-C 5 -C 7 cycloalkyl, optionally substituted with 1 to 3 substituents selected from halo, hydroxyl, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or optionally bridged with a methylene group; or a C 4 -C 6 saturated heterocycle having a hetero atom selected from O, NRa, S, S(═O) 2 ; where Ra is H, C 1 -C 4 alkyl or CH 3 C(═O); R 5 is independently selected from H or methyl; E is —C(═O)—, —S(═O) m —, —NR 5 S(═O) m —, —NR 5 C(═O)—, —OC(═O)—, R 6 is a stable, optionally substituted, monocyclic or bicyclic, carbocycle or heterocycle; m is independently 0,1 or 2; are inhibitors of cathepsin K and useful in the treatment or prophylaxis of osteoporosis.

  化合物II的公式为其中R1和R2中的一个是卤素，另一个是氢或卤素;R3是C1-C4直链或支链，可选择氟代的烷基;R4是氢;或R3与R4和相邻的骨架碳一起定义:一个螺旋C5-C7环烷基，可选地被1至3个取代基所取代，所述取代基选自卤素、羟基、C1-C4烷基或C1-C4卤代烷基;或者可选地通过亚甲基基桥接;或者是一个C4-C6饱和杂环，其中杂原子选自O、NRa、S、S(═O)2;其中Ra是H、C1-C4烷基或CH3C(═O);R5是独立选择的H或甲基;E是—C(═O)—、—S(═O)m—、—NR5S(═O)m—、—NR5C(═O)—、—OC(═O)—;R6是稳定的、可选地取代的、单环或双环、碳环或杂环;m独立地为0、1或2;是猫hepsin K的抑制剂，用于治疗或预防骨质疏松症。
• US7915300B2
  申请人：——

  公开号：US7915300B2

  公开（公告）日：2011-03-29
• 3-Azidotetrahydrofuran-2-carboxylates: monomers for five-ring templated β-amino acid foldamers?
  作者：Mark P Watterson、Lea Pickering、Martin D Smith、Sarah J Hudson、Paul R Marsh、Jacqueline E Mordaunt、David J Watkin、Christopher J Newman、George W.J Fleet

  DOI：10.1016/s0957-4166(99)00205-0

  日期：1999.5

  Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of beta-amino acid oligomers with secondary structure. (C) 1999 Elsevier Science Ltd. All rights reserved.