4-O-[(tert-butyl)diphenylsilyl]-2,3-O-isopropylidene-D-erythrose | 105368-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-[(tert-butyl)diphenylsilyl]-2,3-O-isopropylidene-D-erythrose
• 英文别名: 4-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-D-erythrose；4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-aldehydo-D-erythrose；(4R,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 105368-84-1
• 化学式: C₂₃H₃₀O₄Si
• 分子量: 398.574
• InChiKey: IARLEQVUVIJKBD-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：
  描述：

  4-O-[(tert-butyl)diphenylsilyl]-2,3-O-isopropylidene-D-erythrose 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 萘烷 为溶剂， 反应 5.42h， 生成 {(4R,5S)-5-[(E)-5-(4-Methoxy-benzyloxy)-pent-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol
  参考文献：
  名称：

  Synthetic Study on a 26-Membered Macrolide, Amphidinolide B: Synthesis of the C₁—C₁₃Fragment

  摘要：

  由 D-赤藓酮（3）合成了蚜虫内酯 B 的 C1-C13 片段（1）。埃文斯烷基化反应方案允许在 C11 位置引入立体中心，这一点通过一次 X 射线晶体分析得到了明确证实。

  DOI：

  10.1246/bcsj.71.2433
• 作为产物：
  描述：

  4-O-[(tert-butyl)diphenylsilyl]-2,3-O-isopropylidene-D-erythrose dibenzyl dithioacetal 在 水 、 calcium carbonate 、 mercury dichloride 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以98%的产率得到4-O-[(tert-butyl)diphenylsilyl]-2,3-O-isopropylidene-D-erythrose
  参考文献：
  名称：

  β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives

  摘要：

  The D-manno-configured N-anisylated beta-lactam 40, the beta-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from D-glucose in 8-10 steps, respectively None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the D-erythroses 6, 16, and 17 with the ketene: from mesyloxyacetyl chloride (20) gave the 2-mesyloxy-D-hexono-1,3-lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (> 85%) to the corresponding azides, followed by oxidative N-deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N-atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl)phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the beta-lactam amino acid 43, besides its hydrolysis product 44. Reductive N-acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2-trifluoroacetamido N-(carboxymethyl)-beta-lactam 4 (56%). Similarly, 47 gave the 2-trifluoroacetamide 48 (89%), and hence, the 2-amino-N-(phosphonoylmethyl)-beta-lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected beta-lactams 31a and 35 led to the 2,3-diamino-2,3-dideoxy-D-mannonamides 51 and 53, respectively (Scheme 6).

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2380::aid-hlca2380>3.0.co;2-p

文献信息

• Indium-Mediated Reaction of 1-Bromo-1-nitroalkanes with Aldehydes: Access to 2-Nitroalkan-1-ols
  作者：Raquel G. Soengas、Amalia M. Estévez

  DOI：10.1002/ejoc.201000662

  日期：2010.9

  A novel method for the preparation of 2-nitroalkan-1-ols by an indium-promoted reaction of bromonitromethane with a variety of aldehydes is reported. The reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroalkan-1-ols. The use of chiral sugar-derived aldehydes furnished the corresponding 2-nitroalkan-1-ols with excellent stereoselectivity. The utility of the novel

  报道了一种通过溴硝基甲烷与多种醛的铟促进反应制备 2-nitroalkan-1-ols 的新方法。该反应也用 2-溴-2-硝基丙烷进行，得到 2,2-二烷基-2-硝基烷-1-醇。手性糖衍生醛的使用为相应的 2-nitroalkan-1-ols 提供了出色的立体选择性。新的糖衍生的 2,2-二烷基-2-硝基烷-1-醇用于制备支化亚氨基糖衍生物的效用通过羟甲基支化多羟基化氮杂环庚烷的制备得到证明。
• A NEW TRANSFORMATION OF ALDOSE DERIVED SYNTHONS TO PSEUDO-HEXOPYRANOSE OR PSEUDO-PENTOFURANOSE DERIVATIVES
  作者：Kin-ichi Tadano、Hiroo Maeda、Masahide Hoshino、Youichi Iimura、Tetsuo Suami

  DOI：10.1246/cl.1986.1081

  日期：1986.7.5

  The d-ribose or d-erythrose derived acyclic synthon, which possesses a 2-malonyl carbon chain at C-1 position, was cyclized stereoselectively to a six- or five-membered carbocycle. Those carbocycles were converted into pseudo-β-l-mannopyranose derivatives or pseudo-β-l-arabinofuranose derivatives efficeintly.

  源自于d-核糖或d-赤藓糖的无环合成物，在C-1位拥有一个2-马隆基碳链，经过立体选择性环化形成了六元或五元碳环。这些碳环有效地转化为伪-β-l-甘露糖吡喃糖衍生物或伪-β-l-阿拉伯糖呋喃糖衍生物。
• A novel transformation of four aldoses to some optically pure pseudohexopyranoses and a pseudopentofuranose, carbocyclic analogs of hexopyranoses and pentofuranose. Synthesis of derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes and (1S,2S,3S,4S)-2,3,4-trihydroxy-1(hydroxymethyl)cyclopentane
  作者：Kinichi Tadano、Hiroo Maeda、Masahide Hoshino、Youichi Iimura、Tetsuo Suami

  DOI：10.1021/jo00386a011

  日期：1987.5
• Synthesis of 2-Thioaldoses via BF3-Promoted Cycloaddition of β-Methoxyvinyl Sulfides with 2,3-O-Isopropylidene Derivatives of aldehydo-Aldoses
  作者：Hideyuki Sugimura、Kousuke Kusakabe

  DOI：10.1055/s-0032-1317860

  日期：——

  A highly stereoselective approach to the synthesis of 2-thioaldose derivatives via BF3-promoted cycloaddition of beta-methoxyvinyl sulfides with 2,3-O-isopropylidene derivatives of aldehydo-aldoses is described.
• Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol
  作者：Subhendu Das、Tapan Kumar Kuilya、Rajib Kumar Goswami

  DOI：10.1021/acs.joc.5b00972

  日期：2015.6.19

  A concise and convergent route for stereoselective total synthesis of promising anticancer natural lipid mycalol has been achieved using cheap and readily available L-arabinose as a chiral pool. The notable features of our synthesis comprised regioselective Wacker oxidation, Sharpless asymmetric dihydroxylation, Julia-Kocienski olefination, Wittig olefination, Zipper reaction, and Sonogashira reaction. Comparison of the spectroscopic data on a series of isomers supports the revised structure (Org. Lett. 2015, 17, 1652) instead of the one originally proposed.