tert-butyldimethylsilyl 3-azido-2,3,6-trideoxy-β-L-ribo-hexopyranoside | 203571-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldimethylsilyl 3-azido-2,3,6-trideoxy-β-L-ribo-hexopyranoside
• 英文别名: (2S,3R,4R,6R)-4-azido-6-[tert-butyl(dimethyl)silyl]oxy-2-methyloxan-3-ol
• CAS: 203571-05-5
• 化学式: C₁₂H₂₅N₃O₃Si
• 分子量: 287.434
• InChiKey: PZPUIKSYESHJIF-ZDCRXTMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 3-azido-2,3,6-trideoxy-β-L-ribo-hexopyranoside 在 platinum(IV) oxide 、 Grubbs catalyst first generation lithium aluminium tetrahydride 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 氢气 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 83.0h， 生成 1,4-bis[allyl 3'-trifluoroacetamido-2',3',6'-trideoxy-α-L-ribo-hexopyranos-4'-yl]-1,4-butanediol
  参考文献：
  名称：

  First Preparation of Spacer-Linked Cyclic Neooligoaminodeoxysaccharides

  摘要：

  The preparation of novel cyclic 1,4-butanediol-linked oligoaminodeoxysugars 3-5 and 7 is described which are potential binders to polynucleotides. Neooligosaccharides 3-5 are assembled by two consecutive metathesis protocols. In the first phase metathesis-mediated dimerization of an aminodeoxymonosaccharide which was either allylated at the anomeric center or at C4 led to E/Z mixtures of C-2-symmetric homodimers which were transformed into the corresponding 1,4-butanediol linked disaccharides by catalytic hydrogenation of the central olefinic double bond. Double O-allylation of the head-to-head dimer set the stage for macrocyclization by means of ring-closing metathesis. This ring-closing process was highly dependent of the configuration in the carbohydrate moieties. arabino-Configured homodimer 15 directly yielded the macrocycle 32 which contains two sugar units while under the same metathesis conditions the corresponding ribo-configured starting homodimer 19 afforded cyclic neotetra- and neohexasaccharides 34 and 35 after a preceding dimerization and trimerization step, respectively. In addition, homodimer 23 was coupled with silylglycoside 14a under Lewis-acid promoted glycosidation conditions to furnish the doubly glycosylated homodimer 31. Ring-closing metathesis afforded the macrocyclic neoaminodeoxyoligosaccharide 36 with alternating 1,4-butanediol linkage and glycosidic bond. The primary cyclization products were finally transformed into the respective cyclic neoaminodeoxyoligosaccharides 3-5 and 7 by catalytic hydrogenation and standard deprotection conditions.

  DOI：

  10.1002/1521-3765(20020617)8:12<2717::aid-chem2717>3.0.co;2-p
• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 咪唑 、 sodium azide 、 水 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 56.5h， 生成 tert-butyldimethylsilyl 3-azido-2,3,6-trideoxy-β-L-ribo-hexopyranoside
  参考文献：
  名称：

  A Short and High Yield Access to Glycosyl Donors of Amino-Deoxy-Sugars of Biological Relevance

  摘要：

  Synthesis of silylglycosides of 3-azido-2-deoxy-L-arabino- and ribo-hexopyranoses 4 and 5 has been achieved in 3 steps and 44,6% and 18% overall yields, respectively. The corresponding N-trifluoroacetamido derivatives 9 and 10 were further prepared in 3 steps. Usefulness of 4, 9, and 10 was demonstrated by coupling with epipodophyllotoxin derivatives or with suitably protected aminoacids such as serine or 4-OH-phenylglycine or 4-OH-phenylglycinyl glucoside.

  DOI：

  10.1080/00397919808005074

文献信息

• A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-ε-iso-rhodomycinone
  作者：Bernd Renneberg、Yue-Ming Li、Hartmut Laatsch、Heinz-Herbert Fiebig

  DOI：10.1016/s0008-6215(00)00257-3

  日期：2000.12

  constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-e

  3-氨基-2,3,6-三甲氧基己基吡喃糖是大多数蒽环类抗肿瘤抗生素的重要组成部分。为了研究结构-活性关系，从市售鼠李糖开始以短而有效的途径合成了四种非对映体氨基糖柔红胺，二十二胺，香豆胺和表柔红胺。提供了几种糖基供体，其用途在合成氨糖基-ε-异二十四烯酮中得到了例证。
• A Short and High Yield Access to Glycosyl Donors of Amino-Deoxy-Sugars of Biological Relevance
  作者：Laurent Daley、Carole Mouton、François Tillequin、Elisabeth Seguin、Jean-Claude Florent、Claude Monneret

  DOI：10.1080/00397919808005074

  日期：1998.1

  Synthesis of silylglycosides of 3-azido-2-deoxy-L-arabino- and ribo-hexopyranoses 4 and 5 has been achieved in 3 steps and 44,6% and 18% overall yields, respectively. The corresponding N-trifluoroacetamido derivatives 9 and 10 were further prepared in 3 steps. Usefulness of 4, 9, and 10 was demonstrated by coupling with epipodophyllotoxin derivatives or with suitably protected aminoacids such as serine or 4-OH-phenylglycine or 4-OH-phenylglycinyl glucoside.
• Grynkiewicz; Fokt; Skibicki, Polish Journal of Chemistry, 2005, vol. 79, # 2, p. 335 - 347
  作者：Grynkiewicz、Fokt、Skibicki、Przewloka、Szeja、Priebe

  DOI：——

  日期：——
• First Preparation of Spacer-Linked Cyclic Neooligoaminodeoxysaccharides
  作者：Guang-wu Chen、Andreas Kirschning

  DOI：10.1002/1521-3765(20020617)8:12<2717::aid-chem2717>3.0.co;2-p

  日期：2002.6.17

  The preparation of novel cyclic 1,4-butanediol-linked oligoaminodeoxysugars 3-5 and 7 is described which are potential binders to polynucleotides. Neooligosaccharides 3-5 are assembled by two consecutive metathesis protocols. In the first phase metathesis-mediated dimerization of an aminodeoxymonosaccharide which was either allylated at the anomeric center or at C4 led to E/Z mixtures of C-2-symmetric homodimers which were transformed into the corresponding 1,4-butanediol linked disaccharides by catalytic hydrogenation of the central olefinic double bond. Double O-allylation of the head-to-head dimer set the stage for macrocyclization by means of ring-closing metathesis. This ring-closing process was highly dependent of the configuration in the carbohydrate moieties. arabino-Configured homodimer 15 directly yielded the macrocycle 32 which contains two sugar units while under the same metathesis conditions the corresponding ribo-configured starting homodimer 19 afforded cyclic neotetra- and neohexasaccharides 34 and 35 after a preceding dimerization and trimerization step, respectively. In addition, homodimer 23 was coupled with silylglycoside 14a under Lewis-acid promoted glycosidation conditions to furnish the doubly glycosylated homodimer 31. Ring-closing metathesis afforded the macrocyclic neoaminodeoxyoligosaccharide 36 with alternating 1,4-butanediol linkage and glycosidic bond. The primary cyclization products were finally transformed into the respective cyclic neoaminodeoxyoligosaccharides 3-5 and 7 by catalytic hydrogenation and standard deprotection conditions.