(3aS,6S,6aS)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-6-carbaldehyde | 94840-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,6S,6aS)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-6-carbaldehyde
• CAS: 94840-09-2
• 化学式: C₈H₁₀O₅
• 分子量: 186.164
• InChiKey: QKGJPKFKBNXJLP-SRQIZXRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,6S,6aS)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-6-carbaldehyde 在 borohydride-reduced Pd 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (2S,3S,4R)-2,3-isopropylidenedioxy-4-(4-methoxycarbonylbutyl)-4-butanolide
  参考文献：
  名称：

  A modified synthesis of (+)-biotin from d-glucose

  摘要：

  DOI：

  10.1016/0008-6215(84)85050-8
• 作为产物：
  描述：

  L-古洛糖酸-gamma-内酯 在 水 、 对甲苯磺酸 、 溶剂黄146 、 高碘酸 作用下， 以 四氢呋喃 为溶剂， 反应 36.5h， 生成 (3aS,6S,6aS)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-6-carbaldehyde
  参考文献：
  名称：

  High-Yielding Diastereoselective syn -Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O -Protected Analogues

  摘要：

  A diastereoselective chemoenzymatic synthetic pathway to D‐(+)‐ribono‐1,4‐lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose‐based levoglucosenone (LGO). This route involves a sustainable Baeyer‐Villiger oxidation of LGO to produce enantiopure (S)‐γ‐hydroxymethyl‐α,β‐butenolide (HBO) that is further functionalized with various protecting groups to provide 5‐O‐protected γ‐hydroxymethyl‐α,β‐butenolides. The latter then undergo a diastereoselective and high‐yielding syn‐dihydroxylation of the α,β‐unsaturated lactone moiety followed by a deprotection step to give D‐(+)‐ribono‐1,4‐lactone. Through this 4‐step synthetic route from LGO, D‐(+)‐ribono‐1,4‐lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5‐O‐tert‐butyldimethylsilyl‐, 5‐O‐tert‐butyldiphenylsilyl‐ as well as 5‐O‐benzyl‐ribono‐1,4‐lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.

  DOI：

  10.1002/ejoc.201801780

文献信息

• High-Yielding Diastereoselective <i>syn</i> -Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-<i>O</i> -Protected Analogues
  作者：Maxime Moreaux、Guillaume Bonneau、Aurélien Peru、Fanny Brunissen、Marine Janvier、Arnaud Haudrechy、Florent Allais

  DOI：10.1002/ejoc.201801780

  日期：2019.2.21

  A diastereoselective chemoenzymatic synthetic pathway to D‐(+)‐ribono‐1,4‐lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose‐based levoglucosenone (LGO). This route involves a sustainable Baeyer‐Villiger oxidation of LGO to produce enantiopure (S)‐γ‐hydroxymethyl‐α,β‐butenolide (HBO) that is further functionalized with various protecting groups to provide 5‐O‐protected γ‐hydroxymethyl‐α,β‐butenolides. The latter then undergo a diastereoselective and high‐yielding syn‐dihydroxylation of the α,β‐unsaturated lactone moiety followed by a deprotection step to give D‐(+)‐ribono‐1,4‐lactone. Through this 4‐step synthetic route from LGO, D‐(+)‐ribono‐1,4‐lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5‐O‐tert‐butyldimethylsilyl‐, 5‐O‐tert‐butyldiphenylsilyl‐ as well as 5‐O‐benzyl‐ribono‐1,4‐lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.
• A modified synthesis of (+)-biotin from d-glucose
  作者：T. Ravindranathan、Shivajat V. Hiremath、D. Rajagopala Reddy、A.V. Rama Rao

  DOI：10.1016/0008-6215(84)85050-8

  日期：1984.12