3-O-acetyl-1,2-O-isopropylidene-β-D-altrofuranose | 130995-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-acetyl-1,2-O-isopropylidene-β-D-altrofuranose
• 英文别名: [(3aS,5R,6R,6aS)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 130995-73-2
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: MWHWTXULRQTAPZ-VFCFLDTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-1,2-O-isopropylidene-β-D-altrofuranose 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Applications of Cyclic Sulfates of vic-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars

  摘要：

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.

  DOI：

  10.1021/jo962066b
• 作为产物：
  描述：

  3-O-Acetyl-1,2;5,6-di-O-isopropyliden-β-D-altrose 在 溶剂黄146 作用下， 反应 2.0h， 以84%的产率得到3-O-acetyl-1,2-O-isopropylidene-β-D-altrofuranose
  参考文献：
  名称：

  5,6-二脱氧-5-苯基膦酰基-L-吡喃半乳糖的合成。L-岩藻糖的 P 环糖类似物

  摘要：

  1,2-O-Isopropylidene-3-O-methyl-6-O-tosyl-β-D-arabino-hexofuranos-5-ulose (9a) 及其 3-O-benzyl 同源物 (9b) 由 1, 2:5,6-二-O-异亚丙基-β-D-altrofuranose 分 4 个步骤。在 DBU 存在下将苯基次膦酸甲酯加入 9a 和 9b，然后用 Raney Ni 还原，得到 (5R 和 5S)-5,6-dideoxy-1,2-O-isopropylidene-5-[(甲氧基) 苯基膦基] -3-O-甲基-β-D-阿拉伯-己基呋喃糖（11a）和3-O-苄基同源物（11b），分别。后一化合物(11b)被去苄基化为3-O-未取代的己呋喃糖11d。通过用二氢双（2-甲氧基乙氧基）铝酸钠还原，然后进行酸水解，这些关键中间体 11a、11b 和 11d 提供了标题 L-岩藻糖 13（连同小比例的

  DOI：

  10.1246/bcsj.64.869

文献信息

• HASHIMOTO, HIRONOBU;FUJIMORI, TAKETOSHI;YUASA, HIDEYA, J. CARBOHYDR. CHEM. , 9,(1990) N, C. 683-694
  作者：HASHIMOTO, HIRONOBU、FUJIMORI, TAKETOSHI、YUASA, HIDEYA

  DOI：——

  日期：——
• HANAYA, TADASHI;YAMAMOTO, HIROSHI;OHMAE, TAKESHI;KAWAMOTO, HEIZAN;ARMOUR,+, BULL. CHEM. SOC. JAP., 64,(1991) N, C. 869-876
  作者：HANAYA, TADASHI、YAMAMOTO, HIROSHI、OHMAE, TAKESHI、KAWAMOTO, HEIZAN、ARMOUR,+

  DOI：——

  日期：——
• Applications of Cyclic Sulfates of <i>vic</i>-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars
  作者：Francisco G. Calvo-Flores、Pilar García-Mendoza、Fernando Hernández-Mateo、Joaquín Isac-García、Francisco Santoyo-González

  DOI：10.1021/jo962066b

  日期：1997.6.13

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.
• Synthesis of 5,6-Dideoxy-5-phenylphosphinyl-L-galactopyranoses. The P-in-Ring Sugar Analogs of L-Fucose
  作者：Tadashi Hanaya、Hiroshi Yamamoto、Takeshi Ohmae、Heizan Kawamoto、Margaret-Ann Armour、Alan M. Hogg、Hiroshi Yamamoto

  DOI：10.1246/bcsj.64.869

  日期：1991.3

  debenzylated to 3-O-unsubstituted hexofuranose 11d. By reduction with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by acid hydrolysis, these key intermediates 11a, 11b, and 11d provided the title L-fucoses 13 (together with a minor proportion of D-altropyranoses 14) having as phenylphosphinylidene group in place of the ring oxygen. Compounds 13 and 14 were converted into per-O-acetyl derivatives for

  1,2-O-Isopropylidene-3-O-methyl-6-O-tosyl-β-D-arabino-hexofuranos-5-ulose (9a) 及其 3-O-benzyl 同源物 (9b) 由 1, 2:5,6-二-O-异亚丙基-β-D-altrofuranose 分 4 个步骤。在 DBU 存在下将苯基次膦酸甲酯加入 9a 和 9b，然后用 Raney Ni 还原，得到 (5R 和 5S)-5,6-dideoxy-1,2-O-isopropylidene-5-[(甲氧基) 苯基膦基] -3-O-甲基-β-D-阿拉伯-己基呋喃糖（11a）和3-O-苄基同源物（11b），分别。后一化合物(11b)被去苄基化为3-O-未取代的己呋喃糖11d。通过用二氢双（2-甲氧基乙氧基）铝酸钠还原，然后进行酸水解，这些关键中间体 11a、11b 和 11d 提供了标题 L-岩藻糖 13（连同小比例的