2,3:5,6-di-O-isopropylidene-D-gulitol | 3969-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:5,6-di-O-isopropylidene-D-gulitol
• 英文别名: 5,6-di-O-isopropylidene-D-gulitol；{(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4R,5S)-(5-hydroxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)-methanol；2,3:5,6-Di-O-isopropyliden-D-gulitol；(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 3969-61-7；20581-94-6；71771-89-6；73209-94-6；109008-02-8；120442-06-0；127707-49-7；28910-18-1
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: CKMMCZAVXJINCZ-JXUBOQSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3:5,6-di-O-isopropylidene-D-gulitol 在 吡啶 、 lead(IV) acetate 、 甲醇 、 sodium sulfide 、 sodium tetrahydroborate 、 ammonium sulfate 、 重铬酸吡啶 、 sodium methylate 、 potassium carbonate 、 溶剂黄146 、 间氯过氧苯甲酸 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 130.42h， 生成 (2S,3S,4R,5R)-3,4-bis(tert-butyl-dimethyl-silanyloxy)-5-(2-chloro-6-methylaminopurin-9-yl)tetrahydro-thiophene-2-carboxylic acid methylamide
  参考文献：
  名称：

  N⁶-Substituted D-4‘-Thioadenosine-5‘-methyluronamides:  Potent and Selective Agonists at the Human A₃ Adenosine Receptor

  摘要：

  4'-Thio analogues 3-5 of Cl-IB-MECA (2) (K-i = 1.0 +/- 0.2 nM at the human A(3) adenosine receptor) were synthesized from D-gulono-gamma-lactone via 4-thioribosyl acetate 14 as the key intermediate. All synthesized 4-thionucleosides exhibited higher binding affinity to the human A(3) adenosine receptor than Cl-IB-MECA, among which 4 showed the most potent binding affinity (K-i = 0.28 +/- 0.09 nM). 4 was also selective for A(3) vs human A(1) and human A(2A) receptors by 4800- and 36000-fold, respectively.

  DOI：

  10.1021/jm034098e
• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 生成 2,3:5,6-di-O-isopropylidene-D-gulitol
  参考文献：
  名称：

  与天然葡萄糖苷酶抑制剂salacinol相关的硒和锍离子的设计和合成

  摘要：

  合成了天然存在的葡萄糖苷酶抑制剂 salacinol 的四个系列类似物，用于使用不同的糖苷酶进行结构-活性研究。目标两性离子复合...

  DOI：

  10.1139/v06-100

文献信息

• Purine nucleosides
  申请人：Jeong Shin Lak

  公开号：US20050256143A1

  公开（公告）日：2005-11-17

  Disclosed are purine nucleoside compounds that are selective to A 3 adenosine receptors and are useful for the treatment of cancer and inflammatory diseases. The compounds are shown by the following general formula (I), including isomers thereof: wherein X is sulfur or oxygen; R 1 is hydrogen, alkyl, benzyl, halobenzyl, or phenylalkyl; R 2 is hydrogen, halogen, alkoxy, alkenyl, alkynyl, alkylthio, or thio; R 3 and R 3′ are hydrogen, hydroxyalkyl, alkoxycarbonyl, or alkylaminocabonyl, whereas R 3 and R 3 ′ do not have identical substituents simultaneously; and R 4 is hydrogen or alkyl. Also disclosed are a pharmaceutical composition comprising a compound of formula (I), an isomer, or its pharmacologically acceptable salt as an active ingredient and a method for preventing or treating various diseases, state, or condition, including asthma, inflammation, cerebral ischemia, heart diseases, and cancer.

  揭示了对A3腺苷受体具有选择性的嘌呤核苷化合物，可用于治疗癌症和炎症性疾病。所述化合物由以下一般式（I）表示，包括其异构体：其中X为硫或氧；R1为氢、烷基、苄基、卤代苄基或苯基烷基；R2为氢、卤素、烷氧基、烯基、炔基、烷基硫基或硫基；R3和R3'为氢、羟基烷基、烷氧羰基或烷基氨羰基，其中R3和R3'不同时具有相同的取代基；R4为氢或烷基。还揭示了一种包含一种式（I）的化合物、其异构体或其药理学上可接受的盐作为活性成分的药物组合物，以及一种用于预防或治疗各种疾病、状态或症状的方法，包括哮喘、炎症、脑缺血、心脏疾病和癌症。
• Synthesis of 3-deoxy-2-octulosonic acid derivatives and characterisation of their 3-deoxyoctitols
  作者：Thomas Krülle、Richard R. Schmidt、Helmut Brade、Otto Holst

  DOI：10.1016/0008-6215(94)84248-5

  日期：1994.2

  Abstract The diethyl dithioacetals of d -altrose, d -idose,, and d -talose were used to synthesise the respective O-benzyl aldehydo-sugars as intermediates for the synthesis of 3-deoxy- d -glycero- d -gluco / manno-3-deoxy- d -glycero- l -gulo / ido-, and 3-deoxy- d -glycero- l -allo / altro-octonate derivatives, respectively. After reduction and deprotection, the respective 3-deoxyoctitols were obtained

  摘要用d-altrose，d-idose和d-talose的二乙基二硫缩醛合成了各自的O-苄基醛糖作为中间体，合成了3-deoxy-d-glycero-d-gluco / manno- 3-脱氧-d-甘油-1-古洛糖/碘-和3-脱氧-d-甘油-1-古洛糖/α-辛酸酯衍生物。还原和脱保护后，获得相应的3-脱氧辛醇。为了合成3-脱氧-d-甘油-1-半乳糖/ talo-辛醇，通过还原和选择性氧化转化2,3：5,6-二-O-异亚丙基-d-gulono-1,4-内酯。将C-1转化为醛-d-果糖，由此合成了3-脱氧-d-甘油-1-半乳糖/ talo-辛酸盐。羧基和羰基的还原和脱保护得到3-脱氧辛醇。3-脱氧辛醇通过乙酰化和甲基化形式的GLC和GLC-MS表征。此处提供的数据和较早发布的数据[T. Krulle，O。Holst，H。Brade和RR Schmidt，糖。Res。，247（1993）145
• A new route to some enantiomerically pure substituted morpholines from d-ribono- and d-gulono-1,4-lactones
  作者：Khalil Bennis、Pierre Calinaud、Jacques Gelas、Mebrouk Ghobsi

  DOI：10.1016/0008-6215(94)00190-1

  日期：1994.11

  cyclization compound which gave with tosyl chloride 1,4-anhydro-2,3- O -isopropylidene-5- O -trityl- d -ribitol. The latter was transformed (acid hydrolysis, periodate oxidation, reduction, tritylation, and tosylation) into a ditosylated derivative 16 , which was cyclized into morpholines by the action of primary amines. Acid hydrolysis, followed by acetylation, gives the (2 S )-acetoxymethyl-4-isopropyltetrahydro-1

  摘要d -Ribono-1,4-内酯经缩醛化，三苯甲基化和还原后，生成环化化合物，该化合物与甲苯磺酰氯1,4-脱水-2,3-O-异亚丙基-5-O-三苯甲基-d生成-核糖醇。后者被转化（酸水解，高碘酸盐氧化，还原，三苯甲基化和甲苯磺酸化）成二甲苯磺酰化衍生物16，其在伯胺的作用下环化成吗啉。酸水解，然后乙酰化，得到（2S）-乙酰氧基甲基-4-异丙基四氢-1，4-恶嗪（21）。相似的序列已应用于d-古洛内酯，从而获得了恶嗪33、34和35。
• Heterocyclic compounds for inhibiting virus
  申请人：Monsanto Company

  公开号：EP0322395A1

  公开（公告）日：1989-06-28

  Various heterocyclic compounds, namely (a) the N-methyl derivative of di(hydroxymethyl)-dihydroxy­pyrrolidine, (b) 1,4-dideoxy-1,4-imino-L-arabinitol, (c) 1,4-dideoxy-1,4-imino-L-ribitol, (d) 1,4-dideoxy-1,4-imino-D-ribitol, (e) 1,4-dideoxy-1,4-imino-(N-methyl)-L-arabinitol, (f) 1,4-dideoxy-1,4-imino-(N-methyl)-D-ribitol, (g) 1,4-dideoxy-1,4-benzylimino-L-ribitol, (h) 1,4-dideoxy-1,4-imino-D-talitol, (i) the N-methyl derivative of deoxymannojirimycin, (j) 1,5-dideoxy-1,5-imino-L-fuconolactam, (k) 1,5-dideoxy-1,5-imino-(N-methyl)-L-fucitol, (l) 1,5-dideoxy-1,5-imino-(N-ω-methyl caproate)-L-fucitol, and their pharmaceutically acceptable salt derivatives are useful as inhibiting agents of human immunodeficiency virus. Compounds (a), (e), (j), (k) and (l) are new.

  各种杂环化合物，即 (a) 二（羟甲基）-二羟基吡咯烷的 N-甲基衍生物、 (b) 1,4-二脱氧-1,4-亚氨基-L-阿拉伯糖醇、 (c) 1,4-二脱氧-1,4-亚氨基-L-核糖醇、 (d) 1,4-二脱氧-1,4-亚氨基-D-核糖醇、 (e) 1,4-二脱氧-1,4-亚氨基-(N-甲基)-L-阿拉伯糖醇、 (f) 1,4-二脱氧-1,4-亚氨基-(N-甲基)-D-核糖醇、 (g) 1,4-二脱氧-1,4-苄基亚氨基-L-核糖醇、 (h) 1,4-二脱氧-1,4-亚氨基-D-谷糖醇、 (i) 脱氧曼尻霉素的 N-甲基衍生物、 (j) 1,5-二脱氧-1,5-亚氨基-L-岩藻内酰胺、 (k) 1,5-二脱氧-1,5-亚氨基-(N-甲基)-L-岩藻糖醇、 (l) 1,5-二脱氧-1,5-亚氨基-(N-ω-甲基己酸酯)-L-岩藻糖醇、 及其药学上可接受的盐衍生物可用作人类免疫缺陷病毒的抑制剂。化合物(a)、(e)、(j)、(k)和(l)是新化合物。
• N⁶-Substituted D-4‘-Thioadenosine-5‘-methyluronamides:  Potent and Selective Agonists at the Human A₃ Adenosine Receptor
  作者：Lak Shin Jeong、Dong Zhe Jin、Hea Ok Kim、Dae Hong Shin、Hyung Ryong Moon、Prashantha Gunaga、Moon Woo Chun、Yong-Chul Kim、Neli Melman、Zhan-Guo Gao、Kenneth A. Jacobson

  DOI：10.1021/jm034098e

  日期：2003.8.1

  4'-Thio analogues 3-5 of Cl-IB-MECA (2) (K-i = 1.0 +/- 0.2 nM at the human A(3) adenosine receptor) were synthesized from D-gulono-gamma-lactone via 4-thioribosyl acetate 14 as the key intermediate. All synthesized 4-thionucleosides exhibited higher binding affinity to the human A(3) adenosine receptor than Cl-IB-MECA, among which 4 showed the most potent binding affinity (K-i = 0.28 +/- 0.09 nM). 4 was also selective for A(3) vs human A(1) and human A(2A) receptors by 4800- and 36000-fold, respectively.