(4S,4'S) 4,4'-dimethyl-3,3'4,4'-tetrahydro-6,6'-bi-2H-pyran | 160412-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: (4S,4'S) 4,4'-dimethyl-3,3'4,4'-tetrahydro-6,6'-bi-2H-pyran
• 英文别名: <4S,4'S> 4,4'-dimethyl-3,3'-dihydro-6,6'-bi-2H-pyran；(4S,4'S) 4,4'-dimethyl-3,3'-dihydro-6,6'-bi-2H-pyran；(4S,4'S)-4,4'-dimethyl-3,3',4,4'-tetrahydro-6,6'-bis-2H-pyran；(4S)-4-methyl-6-[(4S)-4-methyl-3,4-dihydro-2H-pyran-6-yl]-3,4-dihydro-2H-pyran
• CAS: 160412-95-3
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: CWDBGXIPPRPSMQ-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S,4'S) 4,4'-dimethyl-3,3'4,4'-tetrahydro-6,6'-bi-2H-pyran 在 camphor-10-sulfonic acid 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 23.0h， 生成 (4S,6S,7R,11S,14R)-14-benzyloxymethyl-4,11-dimethyl-1,8,13,16-tetraoxa-dispiro<5.0.5.4>hexadecane
  参考文献：
  名称：

  Dispiroketals in Synthesis (Part 15): Simultaneous Enantioselective and Regioselective Protection of Glycerol by Reaction with C₂Symmetric (4S,4′S)-Dimethyl-bis-dihydropyran

  摘要：

  甘油通过与(4S,4′S)-4,4′-二甲基-3,3′,4,4′-四氢-6,6′-双-2H-吡喃反应，同时进行对映选择性和区域选择性保护，得到二螺酮产物。

  DOI：

  10.1055/s-1994-25680
• 作为产物：
  描述：

  (4S)-3,4-dihydro-4-methyl-6-tri-n-butylstannyl-2H-pyran 在 双(乙腈)氯化钯(II) 、 正丁基锂 、 copper dichloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以50%的产率得到(4S,4'S) 4,4'-dimethyl-3,3'4,4'-tetrahydro-6,6'-bi-2H-pyran
  参考文献：
  名称：

  Dispiroketals in Synthesis (Part 15): Simultaneous Enantioselective and Regioselective Protection of Glycerol by Reaction with C₂Symmetric (4S,4′S)-Dimethyl-bis-dihydropyran

  摘要：

  甘油通过与(4S,4′S)-4,4′-二甲基-3,3′,4,4′-四氢-6,6′-双-2H-吡喃反应，同时进行对映选择性和区域选择性保护，得到二螺酮产物。

  DOI：

  10.1055/s-1994-25680

文献信息

• Dispiroketals in synthesis (Part 11): Concomitant enantioselective and regioselective protection of 2,5- dibenzoyl-myo-inositol
  作者：Paul J. Edwards、David A. Entwistle、Christophe Genicot、Kun Soo Kim、Steven V. Ley

  DOI：10.1016/0040-4039(94)85337-1

  日期：1994.10

  2,5-Dibenzoyl-myo-inositol, a symmetrical polyol, may be simultaneously enantioselectively and regioselectively protected using the chiral dienes (1), (2) and (3). Deprotection, to afford D or L-1,6-tetra-O-benzyl-myo- inositol (8) and (12) respectively, was achieved using trifluoroacetic acid.

  2,5-二苯甲酰基肌肌醇，对称的多元醇，可以是对映选择性地同时和区域选择性使用手性的二烯烃（保护1），（2）和（3）。脱保护，以得到d或L-1,6-四ö苄基肌-肌醇（8）和（12）分别被实现了使用三氟乙酸。
• Dispiroketals in synthesis (Part 17): Regioselective protection of D-glucopyranoside D-galactopyranoside and D-mannopyranoside substrates.
  作者：Paul J. Edwards、David A. Entwistle、Christophe Genicot、Steven V. Ley、Giuseppina Visentin

  DOI：10.1016/s0957-4166(00)80404-8

  日期：1994.12

  Chiral recognition of enantiomeric trans-1,2-diol relationships leading to regioselective formation of 1,8,13,16-tetraoxadispiro[5.0.5.4] hexadecanes (dispiroketals) of various D-glucopyranoside, D-galactopyranoside and D-mannopyranoside substrates is described. Regioselectivity is achieved using the enantiomerically pure disubstituted tetrahydro-6,6'-bi-2H-pyrans 1, 2, 3, 4 and 5. Facile removal of the dispiroketal protecting group from a number of the sugar adducts has been achieved.
• Dispiroketals in synthesis (part 19)1: Dispiroketals as enantioselective and regioselective protective agents for symmetric cyclic and acyclic polyols.
  作者：Robert Downham、Paul J Edwards、David A Entwistle、Andrew B Hughes、Kun Soo Kim、Steven V Ley

  DOI：10.1016/0957-4166(95)00318-j

  日期：1995.10

  The enantioselective preparation of both enantiomers of a C-2-symmetric diphenyl-bi-dihydropyran 3 and 4 is described. The application of enantiopure bi-dihydropyrans 1 - 4 towards the simultaneous enantioselective differentiation and regioselective protection of a range of cyclic and acyclic symmetrical polyols (23, 37, 43, 45, 54, 61 and 66) is investigated. Several deprotections utilising trifluoroacetic acid (TFA) and a transketalisation with acidic glycerol are presented.
• Dispiroketals in Synthesis (Part 15): Simultaneous Enantioselective and Regioselective Protection of Glycerol by Reaction with C₂Symmetric (4<i>S</i>,4′<i>S</i>)-Dimethyl-<i>bis</i>-dihydropyran
  作者：Christophe Genicot、Steven V. Ley

  DOI：10.1055/s-1994-25680

  日期：——

  Glycerol was simultaneously, enantioselectively and regioselectively protected by reaction with (4S,4′S)-4,4′-dimethyl-3,3′,4,4′-tetrahydro-6,6′-bis-2H-pyran to afford a dispiroketal product.

  甘油通过与(4S,4′S)-4,4′-二甲基-3,3′,4,4′-四氢-6,6′-双-2H-吡喃反应，同时进行对映选择性和区域选择性保护，得到二螺酮产物。