1,2-O-isopropylidene-3,5-di-O-pivaloyl-α-D-xylofuranose | 121200-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3,5-di-O-pivaloyl-α-D-xylofuranose
• 英文别名: 1,2-0-Isopropylidene-3,5-di-0-pivaloyl-α-D-xylofuranose；[(3aR,5R,6S,6aR)-6-(2,2-dimethylpropanoyloxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 2,2-dimethylpropanoate
• CAS: 121200-17-7
• 化学式: C₁₈H₃₀O₇
• 分子量: 358.432
• InChiKey: YHFFWVROODEFBR-YVECIDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3,5-di-O-pivaloyl-α-D-xylofuranose 在 吡啶 、 4-二甲氨基吡啶 、 甲酸 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 、 sodium methylate 、 一水合肼 、 溶剂黄146 作用下， 以 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 29.67h， 生成 6,7-diphenyl-1-(2-deoxy-β-D-threo-pentofuranosyl)lumazine
  参考文献：
  名称：

  Nucleosides. LIV¹Synthesis and Properties of 3′-Azido- and 2′,3′-Dideoxy-6,7-diphenyllumazine Nucleosides

  摘要：

  The best approach for the synthesis of 1-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)lumazine (5) and its 6,7-dimethyl- (4) and 6,7-diphenyl derivatives (3) has been found in the interconversion of the corresponding 1-(2-deoxy-beta-D-threo-pentofuranosyl)-lumazines. Monomethoxytritylation at the 5'-position (1 7, 3 4, 4 9) followed by mesylation at the 3'-OH group and subsequent nucleophilic displacement by lithium azide afforded 1 9, 2 9 and 4 7 which were deprotected by acid treatment to give 3-5 in good yields. The syntheses of 1-(2,3-dideoxy-beta-D- glycero-pentofuranosyl)-6,7-diphenyllumazine (6) and its 6,7-dimethyl derivative (7) were achieved from 1-(2-deoxy-beta-D-erythro-pentofuranosyl)- 6,7-diphenyllumazine and the corresponding 6,7-dimethyllumazine (2 6) via their 5'-O-p-toluoyl- (2 0, 3 0), and 3'-deoxy-3'-iodo derivatives (2 4, 3 1) to form, after radical dehalogenation and final deprotection, 6 and 7. The newly synthesized lumazine nucleosides have been characterized by elemental analyses, UV- and NMR spectra.

  DOI：

  10.1080/15257779408013278
• 作为产物：
  描述：

  三甲基乙酰氯 、 1,2-O-异亚丙基-alpha-D-呋喃木糖 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以29%的产率得到1,2-O-isopropylidene-3,5-di-O-pivaloyl-α-D-xylofuranose
  参考文献：
  名称：

  Chemical process

  摘要：

  本发明涉及一种从起始物D-木糖制造齐多夫定的新合成过程，包括：i）将D-木糖转化为1-（β-D-木糖呋喃基）胸腺嘧啶衍生物；ii）对胸腺嘧啶衍生物进行2'-去氧化作用；以及iii）对2'-去氧化化合物进行3'-叠氮化作用。

  公开号：

  EP0295090A3

文献信息

• 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。
• 1-(.beta.-D-xylofuranosyl)thymine derivatives
  申请人：——

  公开号：US04916218A1

  公开（公告）日：1990-04-10

  This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving: (i) Conversion of D-xylose to a 1-(.beta.-D-xylofuranosyl)thymine derivative; (ii) 2'-Deoxygenation of the thymine derivative; and (iii) 3'-Azidation of the 2'-deoxy compound.

  本发明涉及一种从起始物D-木糖制造齐多夫定的新合成过程，包括：(i) 将D-木糖转化为1-(β-D-木糖呋喃基)胸腺嘧啶衍生物；(ii) 胸腺嘧啶衍生物的2'-去氧化；以及(iii) 2'-脱氧化合物的3'-叠氮化。
• Chemical process
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0295090A3

  公开（公告）日：1990-01-31

  This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving: i) Conversion of D-xylose to a 1-(β-D-xylofuranosyl)thymine derivative;ii) 2′-Deoxygenation of the thymine derivative; andiii) 3′-Azidation of the 2′-deoxy compound.

  本发明涉及一种从起始物D-木糖制造齐多夫定的新合成过程，包括：i）将D-木糖转化为1-（β-D-木糖呋喃基）胸腺嘧啶衍生物；ii）对胸腺嘧啶衍生物进行2'-去氧化作用；以及iii）对2'-去氧化化合物进行3'-叠氮化作用。
• US4916218A
  申请人：——

  公开号：US4916218A

  公开（公告）日：1990-04-10
• Nucleosides. LIV¹Synthesis and Properties of 3′-Azido- and 2′,3′-Dideoxy-6,7-diphenyllumazine Nucleosides
  作者：Xiaodong Cao、Wolfgang Pfleiderer

  DOI：10.1080/15257779408013278

  日期：1994.3

  The best approach for the synthesis of 1-(3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)lumazine (5) and its 6,7-dimethyl- (4) and 6,7-diphenyl derivatives (3) has been found in the interconversion of the corresponding 1-(2-deoxy-beta-D-threo-pentofuranosyl)-lumazines. Monomethoxytritylation at the 5'-position (1 7, 3 4, 4 9) followed by mesylation at the 3'-OH group and subsequent nucleophilic displacement by lithium azide afforded 1 9, 2 9 and 4 7 which were deprotected by acid treatment to give 3-5 in good yields. The syntheses of 1-(2,3-dideoxy-beta-D- glycero-pentofuranosyl)-6,7-diphenyllumazine (6) and its 6,7-dimethyl derivative (7) were achieved from 1-(2-deoxy-beta-D-erythro-pentofuranosyl)- 6,7-diphenyllumazine and the corresponding 6,7-dimethyllumazine (2 6) via their 5'-O-p-toluoyl- (2 0, 3 0), and 3'-deoxy-3'-iodo derivatives (2 4, 3 1) to form, after radical dehalogenation and final deprotection, 6 and 7. The newly synthesized lumazine nucleosides have been characterized by elemental analyses, UV- and NMR spectra.