1,2,5,6-di-O-isopropylidene-3-deoxy-3-amino-α-D-glucofuranoside | 16848-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,5,6-di-O-isopropylidene-3-deoxy-3-amino-α-D-glucofuranoside
• 英文别名: 3-deoxy-3-amino-1,2:5,6-di-O-isopropylidene allofuranoside；3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；3-deoxy-3-amino-1,2:5,6-di-O-isopropylidene-α-D-allofuranose；3-amino-O¹,O²;O⁵,O⁶-diisopropylidene-3-deoxy-α-D-allofuranose；3-Amino-O¹,O²;O⁵,O⁶-diisopropyliden-3-desoxy-α-D-allofuranose；1,2:5,6-di-O-isopropylidene-3-deoxy-3-amino-α-D-allofuranoside；(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-amine
• CAS: 16848-19-4
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: SHQAHGPRANRAGI-VVULQXIFSA-N

物化性质

• 熔点：
  89-91 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  323.5±42.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,5,6-di-O-isopropylidene-3-deoxy-3-amino-α-D-glucofuranoside 在 乙酰氯 吡啶 作用下， 以 甲醇 为溶剂， 反应 42.5h， 生成 methyl 3-amino-3-deoxy-β-D-allopyranoside hydrochloride
  参考文献：
  名称：

  甲基3-氨基-3-脱氧-α-和β-d-吡喃果糖苷和-呋喃呋喃糖苷的合成

  摘要：

  由甲基2-O-苯甲酰基-4,6-O-亚苄基-α-d-吡喃葡萄糖苷按5步顺序合成甲基3-氨基-3-脱氧-α-d-吡喃果糖苷，涉及三氟甲基磺酰化，叠氮化物置换，脱保护，以及催化加氢。用叠氮化四甲基胍取代后，将1,2：5,6-二-O-异亚丙基-α-d-呋喃葡萄糖3-三氟甲磺酸酯提供相应的3-叠氮基-3-脱氧-α-d-呋喃呋喃糖二缩醛，将其转化为3-氨基和3-乙酰氨基产物。叠氮基二缩醛的酸催化甲醇分解得到甲基3-叠氮基-3-脱氧-β-和-α-d-吡喃葡糖苷以及相应的β-d-呋喃呋喃糖苷，吡喃糖苷与呋喃糖苷的比例为3：1。然后通过催化氢化获得两个氨基β-糖苷。

  DOI：

  10.1016/0008-6215(91)80125-7
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 在 lithium aluminium tetrahydride 、 tetramethylguanidinum azide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 1,2,5,6-di-O-isopropylidene-3-deoxy-3-amino-α-D-glucofuranoside
  参考文献：
  名称：

  甲基3-氨基-3-脱氧-α-和β-d-吡喃果糖苷和-呋喃呋喃糖苷的合成

  摘要：

  由甲基2-O-苯甲酰基-4,6-O-亚苄基-α-d-吡喃葡萄糖苷按5步顺序合成甲基3-氨基-3-脱氧-α-d-吡喃果糖苷，涉及三氟甲基磺酰化，叠氮化物置换，脱保护，以及催化加氢。用叠氮化四甲基胍取代后，将1,2：5,6-二-O-异亚丙基-α-d-呋喃葡萄糖3-三氟甲磺酸酯提供相应的3-叠氮基-3-脱氧-α-d-呋喃呋喃糖二缩醛，将其转化为3-氨基和3-乙酰氨基产物。叠氮基二缩醛的酸催化甲醇分解得到甲基3-叠氮基-3-脱氧-β-和-α-d-吡喃葡糖苷以及相应的β-d-呋喃呋喃糖苷，吡喃糖苷与呋喃糖苷的比例为3：1。然后通过催化氢化获得两个氨基β-糖苷。

  DOI：

  10.1016/0008-6215(91)80125-7

文献信息

• MONOSACCHARIDE DERIVATIVES
  申请人：Sattigeri Jitendra Viswajanani

  公开号：US20080114031A1

  公开（公告）日：2008-05-15

  The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection, psoriasis, inflammatory bowel disease, Ulcerative colitis, acne, atherosclerosis, cancer, pruritis and allergic rhinitis. Pharmacological compositions containing compounds disclosed herein and the methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, type I diabetes, psoriasis, allograft rejection, inflammatory bowel disease, Ulcerative colitis, acne, atherosclerosis, cancer, pruritis, allergic rhinitis and other inflammatory and/or autoimmune disorders, using the compounds are also provided.

  本发明涉及单糖衍生物作为抗炎剂。本发明的化合物可用于抑制和预防炎症及相关病理，包括炎症和自身免疫疾病，如支气管哮喘、类风湿性关节炎、I型糖尿病、多发性硬化症、异体移植排斥、银屑病、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、癌症、瘙痒和过敏性鼻炎。还提供了包含本发明披露的化合物的药物组合物，以及使用这些化合物治疗支气管哮喘、慢性阻塞性肺病、类风湿性关节炎、多发性硬化症、I型糖尿病、银屑病、异体移植排斥、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、癌症、瘙痒、过敏性鼻炎以及其他炎症性和/或自身免疫障碍的方法。
• Monosaccharide Derivatives as Anti-Inflammatory and/or Anti-Cancer Agents
  申请人：Sattigeri Vishwajanani Jitendra

  公开号：US20090048186A1

  公开（公告）日：2009-02-19

  The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis and allergic rhinitis. Pharmacological compositions containing compounds disclosed herein and the methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, type I diabetes, psoriasis, allograft rejection, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, cancer, pruritis, allergic rhinitis and other inflammatory and/or autoimmune disorders, using the compounds are also provided.

  本发明涉及单糖衍生物作为抗炎剂。本发明的化合物可用于抑制和预防炎症及相关病理，包括炎症和自身免疫疾病，如支气管哮喘、类风湿性关节炎、I型糖尿病、多发性硬化症、异体移植排斥、银屑病、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、癌症、瘙痒和过敏性鼻炎。还提供了含有本发明披露的化合物的药物组合物，以及使用这些化合物治疗支气管哮喘、慢性阻塞性肺病、类风湿性关节炎、多发性硬化症、I型糖尿病、银屑病、异体移植排斥、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、癌症、瘙痒、过敏性鼻炎以及其他炎症性和/或自身免疫障碍的方法。
• 3-amino-2,3-dideoxy-D-erythro-furanose derivatives
  作者：Minn-Chang Cheng、Keekyung Kim、Yi-Tsong Lin、Janet S. Plummer、Jamil Talhouk、Yan Wang、Tian-Pa You、Harry S. Mosher

  DOI：10.1016/s0040-4020(01)80952-2

  日期：——

  analogs which are modified at the 5-position (5-O-benzoyl, 5-O-trimethylacetyl, the uronic acid and methyl uronate ester). These nitro sugars were conveniently hydrogenated to the corresponding amino sugars 1A–1E. The utility of the trimethylacetyl protecting group has been demonstrated for this sequence of reactions.

  D-木糖已转化为3-硝基-2,3-二脱氧-D-赤藓基呋喃糖苷和几种在5位上修饰的类似物（5-O-苯甲酰基，5-O-三甲基乙酰基，糖醛酸和尿酸甲酯）。这些硝基糖可以方便地氢化为相应的氨基糖1A-1E。已经证明三甲基乙酰基保护基对于该反应序列的效用。
• Monosaccharide derivatives as anti-inflammatory agents
  申请人：Ranbaxy Laboratories Limited

  公开号：EP1953170A1

  公开（公告）日：2008-08-06

  The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disclosed herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory, cancer, cardiovascular and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type-I diabetes, multiple sclerosis, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, pruritis or allergic rhinitis. Pharmacological compositions containing compounds disclosed herein and the methods of treating diseases such as bronchial asthma, rheumatoid arthritis, type-I diabetes, multiple sclerosis, cancer, cardiovascular diseases, allograft rejection, psoriasis, inflammatory bowel disease, ulcerative colitis, acne, atherosclerosis, pruritis or allergic rhinitis and other inflammatory and/or autoimmune disorders, using the compounds are also provided.

  本发明涉及单糖衍生物作为抗炎药剂。本文披露的化合物可用于抑制和预防炎症及相关病理，包括炎症性、癌症、心血管和自身免疫疾病，如支气管哮喘、类风湿关节炎、I型糖尿病、多发性硬化症、移植排斥、牛皮癣、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、瘙痒或过敏性鼻炎。还提供了含有本文披露的化合物的药理组合物和治疗支气管哮喘、类风湿关节炎、I型糖尿病、多发性硬化症、癌症、心血管疾病、移植排斥、牛皮癣、炎症性肠病、溃疡性结肠炎、痤疮、动脉粥样硬化、瘙痒或过敏性鼻炎等疾病的方法，以及使用这些化合物治疗其他炎症性和/或自身免疫性疾病的方法。
• Regioselective synthesis of chiral six- and seven-membered N-heterocycles from N-allyl carbohydrate nitrones: Tuning of regioselectivity by N-substitution
  作者：Swapan Majumdar、Anup Bhattacharjya、Amarendra Patra

  DOI：10.1016/s0040-4020(99)00694-8

  日期：1999.10

  The intramolecular cycloaddition of N-allyl carbohydrate nitrones leads to enantiomerically pure six- and seven-membered nitrogen heterocycles and the regioselectivity of the cycloaddition was controlled by changing the substituent on the nitrogen atom of the N-allyl moiety.

  N-烯丙基碳水化合物硝酮的分子内环加成导致对映体纯的六元和七元氮杂环，并且通过改变N-烯丙基部分的氮原子上的取代基来控制环加成的区域选择性。