3-azido-3-deoxy-1,2-O-isopropylidene-6-O-benzoyl-α-D-glucofuranose | 68115-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-azido-3-deoxy-1,2-O-isopropylidene-6-O-benzoyl-α-D-glucofuranose
• 英文别名: 3-azido-6-O-benzoyl-3-deoxy-1,2-O-isopropylidene-α-D-gluco-pentofuranose；1,2-O-isopropylidene-6-O-benzoyl-3-azido-3-deoxy-α-D-glucofuranose；[(2R)-2-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] benzoate
• CAS: 68115-75-3
• 化学式: C₁₆H₁₉N₃O₆
• 分子量: 349.343
• InChiKey: MHVGFSZHLAGWIT-WPLOAARJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-azido-3-deoxy-1,2-O-isopropylidene-6-O-benzoyl-α-D-glucofuranose 以 dioxane-water 为溶剂， 生成 6-O-benzoyl-3-azido-3-deoxy-D-glucofuranose
  参考文献：
  名称：

  2-Substituted arabinofuranosyl nucleosides and nucleotides

  摘要：

  具有2'-azido、2'-amino或2'-烃基氨基取代基的新型阿拉伯糖呋喃核苷和核苷酸具有抗肿瘤、抗病毒和抗微生物特性，其制备方法为将嘧啶、嘌呤或1,3-噁二唑碱基与酰化的2-azido-2-脱氧阿拉伯糖呋喃基卤代物缩合，然后去保护基并进行催化氢化，必要时将2'-azido基转化为2'-amino基，并且，如果需要，进行烷基化等反应将2'-amino基转化为2'-烃基氨基基团。

  公开号：

  US04230698A1
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium azide 、 磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 16.0h， 生成 3-azido-3-deoxy-1,2-O-isopropylidene-6-O-benzoyl-α-D-glucofuranose
  参考文献：
  名称：

  An Alternative Synthesis of the Antineoplastic Nucleoside 4‘-ThioFAC and Its Application to the Synthesis of 4‘-ThioFAG and 4‘-Thiocytarazid

  摘要：

  Previously, we synthesized 4'-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method far the synthesis of 4'-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the I-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a beta-anomer of 4'-thioFAC. The reaction of 2,6-diaminopurine with the I-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a beta-anomer of 4'-thioFAG, a guanine congener of 4'-thioFAC, selectively. Using a similar approach, we synthesized 4'-thiocytarazid, which was not possible using the original method.

  DOI：

  10.1021/jo990958g

文献信息

• Synthetic Studies on 2′-Substituted-4′-thiocytidine Derivatives as Antineoplastic Agents
  作者：Yuichi Yoshimura、Mikari Endo、Kenji Kitano、Kohei Yamada、Shinji Sakata、Shinji Miura、Haruhiko Machida

  DOI：10.1080/15257779908041569

  日期：1999.4

  As potential antineoplastic agents, we have synthesized 4'-thioFAC and 4'-thiocytarazid by developing an alternative synthetic method. 4'-ThioFAC showed potent antineoplastic activities in vivo as well as in vitro.
• The effect of substituting key hydroxyl groups by amino groups on the binding of the Lewis b tetrasaccharide by a lectin and a monoclonal antibody
  作者：Raymond U. Lemieux、Roman Szweda、Eugenia Paszkiewicz-Hnatiw、Ulrike Spohr

  DOI：10.1016/0008-6215(90)80170-8

  日期：1990.9
• LEMIEUX, RAYMOND U.;SZWEDA, ROMAN;PASZKIEWICZ-HNATIW, EUGENIA;SPOHR, ULRI+, CARBOHYDR. RES., 205,(1990) C12-C18
  作者：LEMIEUX, RAYMOND U.、SZWEDA, ROMAN、PASZKIEWICZ-HNATIW, EUGENIA、SPOHR, ULRI+

  DOI：——

  日期：——
• BOBEK, M. V.;BLOCH, A.;CHENG, YUNG-CHI
  作者：BOBEK, M. V.、BLOCH, A.、CHENG, YUNG-CHI

  DOI：——

  日期：——
• US4230698A
  申请人：——

  公开号：US4230698A

  公开（公告）日：1980-10-28