D-erythrose propane-1,3-diyl dithioacetal | 218439-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: D-erythrose propane-1,3-diyl dithioacetal
• 英文别名: (1R,2R)-1-(1,3-dithian-2-yl)propane-1,2,3-triol
• CAS: 218439-29-3
• 化学式: C₇H₁₄O₃S₂
• 分子量: 210.318
• InChiKey: OVAFLAQRXUIAPF-PHDIDXHHSA-N

物化性质

• 沸点：
  481.8±40.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-erythrose propane-1,3-diyl dithioacetal 在 sodium hydride 、 copper(II) sulfate 作用下， 反应 9.0h， 生成 3,4-O-Isopropyliden-2-O-<(methylthio)thiocarbonyl>-D-erythrose-trimethylendithioacetal
  参考文献：
  名称：

  Paulsen, Hans; Roden, Klaus; Sinnwell, Volker, Liebigs Annalen der Chemie, 1981, # 11, p. 2009 - 2027

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-丙二硫醇 、 (2R,3R)-2,3,4-三羟基丁醛 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到D-erythrose propane-1,3-diyl dithioacetal
  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

文献信息

• β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives
  作者：Thomas Storz、Bruno Bernet、Andrea Vasella

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

  日期：1999.12.15

  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).
• Paulsen, Hans; Roden, Klaus; Sinnwell, Volker, Liebigs Annalen der Chemie, 1981, # 11, p. 2009 - 2027
  作者：Paulsen, Hans、Roden, Klaus、Sinnwell, Volker、Luger, Peter

  DOI：——

  日期：——
• Synthetic Study on a 26-Membered Macrolide, Amphidinolide B: Synthesis of the C₁—C₁₃Fragment
  作者：Katsuhide Ohi、Kyoko Shima、Kozue Hamada、Yoshio Saito、Naoki Yamada、Shigeru Ohba、Shigeru Nishiyama

  DOI：10.1246/bcsj.71.2433

  日期：1998.10

  The C1—C13 fragment of amphidinolide B (1) was synthesized from D-erythrose (3). The Evans alkylation reaction protocol allowed the introduction of the stereogenic center at the C11 position, which was unambiguously confirmed by a single X-ray crystallographic analysis.

  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。