O¹,O²;O⁵,O⁶-diisopropylidene-O³,O⁴-dimethyl-D-mannitol | 71240-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O¹,O²;O⁵,O⁶-diisopropylidene-O³,O⁴-dimethyl-D-mannitol
• 英文别名: (4R)-4-[(1R,2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-dimethoxyethyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 71240-64-7
• 化学式: C₁₄H₂₆O₆
• 分子量: 290.357
• InChiKey: GGHPDYIXBIBFTP-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O¹,O²;O⁵,O⁶-diisopropylidene-O³,O⁴-dimethyl-D-mannitol 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 生成 O³,O⁴-dimethyl-D-mannitol
  参考文献：
  名称：

  Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes

  摘要：

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.

  DOI：

  10.1055/s-0033-1338865
• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 O¹,O²;O⁵,O⁶-diisopropylidene-O³,O⁴-dimethyl-D-mannitol
  参考文献：
  名称：

  Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes

  摘要：

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.

  DOI：

  10.1055/s-0033-1338865

文献信息

• Selective deprotection of an acetal group in monosaccharide derivatives and related compounds using Me3SiCH2MgCl
  作者：Yu-Huei Chen、Yueh-Ting Tseng、Tien-Yau Luh

  DOI：10.1039/cc9960000327

  日期：——

  Treatment of an acetal of a contiguous diol with Me3SiCH2MgCl liberates the corresponding diol regioselectively; chelation is used to rationalize the selectively.

  用Me3SiCH2MgCl处理相邻二醇的缩醛可以有选择性地释放出相应的二醇；配位作用被用来合理化这种选择性。
• Diastereoselective Grignard Additions to <i>O</i>-Protected Polyhydroxylated Ketones:  A Reaction Controlled by Groundstate Conformation?
  作者：Johann Mulzer、Catarina Pietschmann、Jürgen Buschmann、Peter Luger

  DOI：10.1021/jo961542v

  日期：1997.6.13

  The O-protected polyhydroxy ketones 9-14 and 39, 42 add sigma-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-28 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the ''top face'' of the carbonyl group is much less shielded than the ''bottom'' face. Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.
• Selective Deprotection of Acetals with Me₃SiCH₂MgCl. Peterson-Type Olefination of Acetals
  作者：Chao-Cheng Chiang、Yu-Huei Chen、Yu-Tsai Hsieh、Tien-Yau Luh

  DOI：10.1021/jo000317h

  日期：2000.7.1

  By employing the chelation strategy, treatment of an acetal of a contiguous diol with Me3SiCH2MgCl liberates the corresponding diol regioselectively. In addition, acetals of different structural variety are transformed upon treatment with Me2SiCH2MgCl and ZnI2 into the corresponding olefination products in good yield.
• 3,4-di-O-alkylhexitol derivatives containing biological alkylating groups at C-1 and C-6
  作者：János Kuszmann

  DOI：10.1016/s0008-6215(00)86066-8

  日期：1979.6
• Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes
  作者：Scott Snyder、Alexandria Brucks、Daniel Treitler、Shu-An Liu

  DOI：10.1055/s-0033-1338865

  日期：——

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.