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2-O-acetyl-1,5-anhydro-3,4-dideoxy-6-O-[(1,1-dimethyl)ethyldimethyl]silyl-D-erythro-hexitol | 216098-96-3

中文名称
——
中文别名
——
英文名称
2-O-acetyl-1,5-anhydro-3,4-dideoxy-6-O-[(1,1-dimethyl)ethyldimethyl]silyl-D-erythro-hexitol
英文别名
[(3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]oxan-3-yl] acetate
2-O-acetyl-1,5-anhydro-3,4-dideoxy-6-O-[(1,1-dimethyl)ethyldimethyl]silyl-D-erythro-hexitol化学式
CAS
216098-96-3
化学式
C14H28O4Si
mdl
——
分子量
288.459
InChiKey
YYKVUMKVSHOJQE-QWHCGFSZSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.12
  • 重原子数:
    19
  • 可旋转键数:
    6
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.93
  • 拓扑面积:
    44.8
  • 氢给体数:
    0
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Synthesis of Methylene-Expanded 2‘,3‘-Dideoxyribonucleosides
    摘要:
    A method for the preparation of methylene-expanded 2',3'-dideoxyribonucleosides is reported. The very inexpensive starting material levoglucosenone 8 was converted into the known mixture of alcohols 12ab which were converted into the required silyl ether alcohol 26 in six steps via either of two routes. The first involved a one-step acetylation and opening of the anhydro sugar bridge to give the triacetates 20ab which were reduced with triethylsilane and silyl triflate to afford the diacetates 21ab, both of which gave 26 after further functional group conversions. The second route entailed a simple acetylation of 12ab followed by reduction with triethylsilane and silyl triflate to give the monoacetates 19ab, both converted via straightforward chemistry into 26. Mesylation of the alcohol of 26 furnished the mesylate 27. Alkylation of adenine with the mesylate 27 afforded the silyl ether 28 which was deprotected to give the desired modified dideoxy nucleoside 7a. Alkylation of 2,6-diaminopurine 38 with the mesylate gave the protected diaminopurine nucleoside 39. Upon acetylation, it produced a mixture of di- and monoacetates 40-41, the latter of which was transformed into the desired guanosine analogue 7e. Thus, two new nucleoside analogues 7ae were prepared from levoglucosenone 8.
    DOI:
    10.1021/jo980436l
  • 作为产物:
    描述:
    2-O-acetyl-1,6-anhydro-3,4-dideoxy-β-D-threo/erythro-hexopyranose 在 咪唑三乙基硅烷三氟甲磺酸三甲基硅酯 作用下, 以 N,N-二甲基甲酰胺乙腈 为溶剂, 生成 2-O-acetyl-1,5-anhydro-3,4-dideoxy-6-O-[(1,1-dimethyl)ethyldimethyl]silyl-D-erythro-hexitol
    参考文献:
    名称:
    Synthesis of Methylene-Expanded 2‘,3‘-Dideoxyribonucleosides
    摘要:
    A method for the preparation of methylene-expanded 2',3'-dideoxyribonucleosides is reported. The very inexpensive starting material levoglucosenone 8 was converted into the known mixture of alcohols 12ab which were converted into the required silyl ether alcohol 26 in six steps via either of two routes. The first involved a one-step acetylation and opening of the anhydro sugar bridge to give the triacetates 20ab which were reduced with triethylsilane and silyl triflate to afford the diacetates 21ab, both of which gave 26 after further functional group conversions. The second route entailed a simple acetylation of 12ab followed by reduction with triethylsilane and silyl triflate to give the monoacetates 19ab, both converted via straightforward chemistry into 26. Mesylation of the alcohol of 26 furnished the mesylate 27. Alkylation of adenine with the mesylate 27 afforded the silyl ether 28 which was deprotected to give the desired modified dideoxy nucleoside 7a. Alkylation of 2,6-diaminopurine 38 with the mesylate gave the protected diaminopurine nucleoside 39. Upon acetylation, it produced a mixture of di- and monoacetates 40-41, the latter of which was transformed into the desired guanosine analogue 7e. Thus, two new nucleoside analogues 7ae were prepared from levoglucosenone 8.
    DOI:
    10.1021/jo980436l
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顺式-环氧丙烷-3,4-二胺二盐酸盐 顺式-2-(碘甲基)-3-羟基四氢呋喃 顺式-2-(碘甲基)-3-羟基四氢呋喃 青榄呋喃 茶香螺烷 苯胺,4-(2-哌嗪基)- 碳氯灵 硼烷四氢呋喃络合物 硫丹乙酯 甲基甲丙烯酰酸酯-叔丁基甲丙烯酰酸酯-月桂基甲丙烯酰酸酯共聚物 甲基丙烯酸四氢糠基酯 甲基[(噁戊环-2-基)甲基]胺盐酸 甲基2,5-脱水-3-脱氧戊酮酸酯 甲基(四氢呋喃-2-基甲基)砜 牛蝇畏 溴化锰(II)双(四氢呋喃) 溴化亚铁(II),双(四氢呋喃) 氧化芳樟醇 氘代四氢呋喃 异硫氰酸氢糠酯 异丙基-(四氢-呋喃-2-甲基)-胺 失水山梨醇 四氯双(四氢呋喃)合铌(IV) 四氢糠醇乙酸酯 四氢糠醇丙酸酯 四氢糠醇 四氢糠基硫醇 四氢呋喃氯化钛 四氢呋喃-D4 四氢呋喃-3-甲醛 四氢呋喃-2-甲醛 四氢呋喃-2-甲酰肼盐酸盐 四氢呋喃-2-乙酸 四氢呋喃 四氢-alpha-戊基-2-呋喃乙醇乙酸酯 四氢-alpha-[2-(四氢呋喃-2-基)乙基]-2-呋喃-1-丙醇 四氢-alpha,alpha,5-三甲基-5-乙烯基糠基乙酸酯 四氢-alpha,alpha,5-三甲基-5-(4-甲基-3-环己烯-1-基)呋喃-2-甲醇 四氢-N-[(四氢-2-呋喃基)甲基]-2-呋喃甲胺 四氢-N,2-二甲基-2-糠基胺 四氢-Alpha-戊基-2-呋喃甲醇乙酸酯 四氢-5-羟基呋喃-2-甲醇 四氢-5-甲基呋喃-2-甲醇 四氢-2-辛基呋喃 四氢-2-甲基-2-呋喃醇 四氢-2-呋喃基甲基3-氯丙酸酯 四氢-2-呋喃基氯乙酸甲酯 四氢-2-呋喃丙醇 四氢-2-呋喃-1-丙醇丙酸酯 呋喃,2-(二氯甲基)四氢-