(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-methane β anomer | 95189-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-methane β anomer
• 英文别名: β-1,5-anhydro-2,3,4,6-tetra-O-benzyl-C-methyl-D-glucitol；3,4,5,7-Tetra-O-benzyl-2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptitol；2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-heptitol；(2S,3S,4R,5R,6R)-2-methyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 95189-55-2
• 化学式: C₃₅H₃₈O₅
• 分子量: 538.684
• InChiKey: WIWPUDCFWHDUNF-BGXBPKQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-内酯 在 镍 氢气 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-methane β anomer
  参考文献：
  名称：

  Unusual behaviour of some γ- and δ-lactones towards dichloromethylenation using tris(dimethylamino)phosphine–tetrachloromethane

  摘要：

  Lactones derived from D-glucose, D-mannose and L-ascorbic acid reacted unexpectedly with tris-(dimethylamino)phosphine-tetrachloromethane to give, respectively, dichloroalkene, anomeric vinyl chloride or acyl chloride; this behaviour supports an ionic mechanism for the alkenation.

  DOI：

  10.1039/p19920001471

文献信息

• Organometallics in organic synthesis. Applications of a new diorganozinc reaction to the synthesis of C-glycosyl compounds with evidence for an oxonium-ion mechanism
  作者：Alan P. Kozikowski、Toshiro Konoke、Allen Ritter

  DOI：10.1016/s0008-6215(00)90882-6

  日期：1987.12

  features of a new organozinc-based substitution process [heteroatom-C-(R1,R2)-SPh + R3(2)Zn----heteroatom-C-(R1,R2,R3)], first discovered during a total synthesis of the alkaloid mycotoxin alpha-cyclopiazonic acid, are described. Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process. Since these sulfur compounds are converted into C-glycosyl compounds with some

  首次发现新的基于有机锌的取代过程[杂原子-C-（R1，R2）-SPh + R3（2）Zn ----杂原子-C-（R1，R2，R3）]的机理和立体化学特征在生物碱真菌毒素的全合成过程中，描述了α-环吡嗪酸。苯基硫代糖苷是研究该反应过程性质的有价值的底物。由于这些硫化合物以一定的立体选择性转化为C-糖基化合物，因此有机锌化学确实为这些生物活性物质提供了新的进入途径。
• Stable C-Glycoside Sugar and C-Glycoconjugate Mimetics, Method for preparing same and uses Thereof in Particular in Cosmetics and Drugs
  申请人：Castelot-Deliencourt-Godefroy Géraldine

  公开号：US20090318678A1

  公开（公告）日：2009-12-24

  The invention concerns a C-glycoside compound of formula (I); wherein: n is equal to 1 or 2; Y represents H or halogen; X is an alkyl chain bearing at least one amino, amide, acid, ester, carbonyl, alcohol, aryl function or a carbonyl, ester amide, amino, alcohol group; the R's, identical or different, represent a OH or OR′ group where R′ is an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl group or one or more sugars; R1 represents OR′, NR″R″′, N3, or a phthalamide with R″ and R″′, identical or different, represent H or an alkyl, aryl, benzyl, benzoyl, acetyl, alkoxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl group; R2 represents H or halogen or a OH, OR, NR″R″′ or N3 group, as well as derivatives thereof in physiologically or pharmaceutically acceptable base, mineral or organic acid-addition salt, hydrate or solvate form. The invention is useful for preparing C-glycoside compounds or C-glycoconjugates applicable in particular in cosmetology, medical imagery, immunology for treating cancer, diabetes, hypertension.

  本发明涉及一种化学式(I)的C-葡萄糖苷化合物；其中：n等于1或2；Y代表H或卤素；X是一个带有至少一个氨基、酰胺、酸、酯、酰基、醇、芳基功能或一个酰基、酯酰胺、氨基、醇基的烷基链；R，相同或不同，代表OH或OR′基团，其中R′是一个烷基、苄基、苯甲酰基、乙酰基、偏戊酰基、三烷基硅基、叔丁基二苯基硅基团或一个或多个糖；R1代表OR′、NR″R″′、N3或具有R″和R″′相同或不同的邻苯二甲酰胺，其中R″和R″′代表H或一个烷基、芳基、苄基、苯甲酰基、乙氧羰基、烯丙氧羰基、苄氧羰基团；R2代表H或卤素或一个OH、OR、NR″R″′或N3基团，以及其在生理学或药学上可接受的碱、矿物酸或有机酸盐、水合物或溶剂化合物形式的衍生物。本发明用于制备C-葡萄糖苷化合物或C-葡糖结合物，特别适用于化妆品学、医学影像学、免疫学以治疗癌症、糖尿病、高血压。
• Reactions of glycosyl fluorides. Synthesis of C-glycosides
  作者：K. C. Nicolaou、Roland E. Dolle、Alexander Chucholowski、Jared L. Randall

  DOI：10.1039/c39840001153

  日期：——

  Glycosyl fluorides were found to react with a number of nucleophilic reagents with or without catalysis leading to a variety of C-glycosides and related compounds.

  发现糖基氟化物在催化作用或不催化作用下与许多亲核试剂反应，从而导致多种C-糖苷和相关化合物。
• TETRAHYDROPYRAN NUCLEIC ACID ANALOGS
  申请人：Swayze Eric E.

  公开号：US20090092981A1

  公开（公告）日：2009-04-09

  The present disclosure describes tetrahydropyran nucleoside analogs, oligomeric compounds prepared therefrom and methods of using the oligomeric compounds. More particularly, tetrahydropyran nucleoside analogs are provided, having one or more chiral substituents, that are useful for enhancing properties of oligomeric compounds including nuclease resistance and binding affinity. In some embodiments, the oligomeric compounds provided herein hybridize to a portion of a target RNA resulting in loss of normal function of the target RNA.

  本公开描述了四氢吡喃核苷类似物，以及由此制备的寡聚合物化合物和使用这些寡聚合物化合物的方法。更具体地说，提供了具有一个或多个手性取代基的四氢吡喃核苷类似物，这些类似物可用于增强包括核酸酶抗性和结合亲和性在内的寡聚合物化合物的性质。在某些实施例中，本文提供的寡聚合物可以与目标RNA的部分杂交，导致目标RNA失去正常功能。
• NOVEL GEM-DIFLUORINATED C-GLYCOSIDE COMPOUNDS DERIVED FROM PODOPHYLLOTOXIN, THEIR PREPARATION AND THEIR APPLICATIONS
  申请人：Quirion Jean-Charles

  公开号：US20090318675A1

  公开（公告）日：2009-12-24

  The invention relates to a gem-difluoride glycoconjugated compound with formula (I): where R represents II or a benzyl, acetyl, benzoyl alkyl group, R 1 and R 2 may be identical or different and represent H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl, tertiobutyldiphenylsilyl protective group or an acetal group of the CR′R′ type, where R′ and R′ may be identical or different and represent H or an alkyl, aryl, benzyl or thiophene group, R 3 represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, R 4 represents OR″, NGR′GR′, N 3 , or a phthalimide, where R″ represents H or an alkyl, benzyl, benzoyl, acetyl, pivaloyl, trialkylsilyl or tertiobutyldiphenylsilyl protective group, GR′ and GR′ may be identical or different and represent II or an alkyl, benzyl, benzoyl, acetyl, alkyloxycarbonyl, allyloxycarbonyl or benzyloxycarbonyl group, R 5 represents a free or protected hydroxyl group or a halogen, R 6 represents H or an alkyl, acetyl, benzyl, PO 3 H or PO 3 Na group. It is applicable to the preparation of compounds that can be used particularly for the treatment of cancer.

  这项发明涉及一种具有化学式(I)的双氟甘露聚糖结合化合物，其中R代表II或苄基、乙酰基、苯甲酰基烷基，R1和R2可以相同也可以不同，代表H或烷基、苄基、苯甲酰基、乙酰基、戊酰基、三烷基硅基、叔丁基二苯基硅基保护基或CR′R′型的缩醛基团，其中R′和R′可以相同也可以不同，代表H或烷基、芳基、苄基或噻吩基，R3代表H或烷基、苄基、苯甲酰基、乙酰基、戊酰基、三烷基硅基或叔丁基二苯基硅基保护基，R4代表OR″、NGR′GR′、N3或邻苯二甲酰亚胺，其中R″代表H或烷基、苄基、苯甲酰基、乙酰基、戊酰基、三烷基硅基或叔丁基二苯基硅基保护基，GR′和GR′可以相同也可以不同，代表II或烷基、苄基、苯甲酰基、乙酰基、烷氧羰基、烯丙氧羰基或苄氧羰基，R5代表自由或受保护的羟基或卤素，R6代表H或烷基、乙酰基、苄基、PO3H或PO3Na基团。该发明适用于制备特别用于癌症治疗的化合物。