O⁵,O⁶-isopropylidene-D-gulonic acid-4-lactone | 67321-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O⁵,O⁶-isopropylidene-D-gulonic acid-4-lactone
• 英文别名: O⁵,O⁶-Isopropyliden-D-gulonsaeure-4-lacton；5,6-O-isopropylidene-D-gulonic acid γ-lactone；5,6-O-Isopropylidene-D-gulonic acid gamma-lactone；(3R,4S,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one
• CAS: 67321-94-2
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: JNTPPVKRHGNFKM-UCROKIRRSA-N

物化性质

• 熔点：
  166-170 °C
• 沸点：
  355.7±42.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O⁵,O⁶-isopropylidene-D-gulonic acid-4-lactone 在 吡啶 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carboxylate
  参考文献：
  名称：

  Synthesis of all diastereomeric methyl 2,5-anhydro-3-deoxy-hexonates: precursors to C-2-deoxynucleosides and THF-templated γ- and δ-amino acids

  摘要：

  Efficient syntheses of all diastereomers of methyl 2,5-anhydro-3-deoxy-hexonate from mannono- or gulono-lactones provide precursors for C-nucleosides of 2-deoxyribose and for THF-templated gamma- and delta-amino acids. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01416-3
• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 盐酸 、 丙酮 作用下， 生成 O⁵,O⁶-isopropylidene-D-gulonic acid-4-lactone 、 2,3,5,6-di-O-isopropylidene-D-gulono-1,4-lactone
  参考文献：
  名称：

  Acetonderivate der Monosaccharide. I. Diaceton-d-gulose

  摘要：

  DOI：

  10.1246/bcsj.18.226

文献信息

• SUBSTITUTED NUCLEOSIDE DERIVATIVES USEFUL AS ANTICANCER AGENTS
  申请人：Pfizer Inc.

  公开号：US20160244475A1

  公开（公告）日：2016-08-25

  Compounds of the general formula (I): processes for the preparation of these compounds, compositions containing these compounds, and the uses of these compounds.

  通式（I）的化合物： 制备这些化合物的方法，含有这些化合物的组合物，以及这些化合物的用途。
• [EN] METHODS FOR THE PREPARATION OF (3R,3aS,6aR) HEXAHYDRO-FURO[2,3-b]FURAN-3-OL<br/>[FR] PROCEDES DE PREPARATION DE (3R,3AS,6AR)HEXAHYDRO-FURO[2,3-B]FURAN-3-OL
  申请人：TIBOTEC PHARM LTD

  公开号：WO2005095410A1

  公开（公告）日：2005-10-13

  The present invention relates to methods for the preparation of diastereomerically pure (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol (6) as well as a novel intermediate, (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one (4) for use in said methods. More in particular the invention relates to a stereoselective method for the preparation of diastereomerically pure (3R,3aS,6aR) hexahydro-furo[2,3-b]furan-3-ol, as well as methods for the crystallization of (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan- 2-one and for the epimerization of (3aR,4R,6aS) 4-methoxy-tetrahydro-furo[3,4-b]-furan-2-one to (3aR,4S,6aS) 4-methoxy-tetrahydro-furo[3,4-b]furan-2-one.

  本发明涉及制备对映异构体纯度高的(3R,3aS,6aR)六氢呋喃[2,3-b]呋喃-3-醇（6）的方法，以及用于该方法的新型中间体(3aR,4S,6aS) 4-甲氧基四氢呋喃[3,4-b]呋喃-2-酮（4）。更具体地说，本发明涉及一种立体选择性的制备对映异构体纯度高的(3R,3aS,6aR)六氢呋喃[2,3-b]呋喃-3-醇的方法，以及用于(3aR,4S,6aS) 4-甲氧基四氢呋喃[3,4-b]呋喃-2-酮的结晶方法和(3aR,4R,6aS) 4-甲氧基四氢呋喃[3,4-b]-呋喃-2-酮的外消旋化为(3aR,4S,6aS) 4-甲氧基四氢呋喃[3,4-b]呋喃-2-酮的方法。
• [EN] METHOD FOR THE PREPARATION OF HEXAHYDRO-FURO[2,3-B]FURAN-3-OL<br/>[FR] PROCEDE DE PREPARATION D'UN HEXAHYDRO-FURO[2,3-B]FURANE-3-OL
  申请人：TIBOTEC PHARM LTD

  公开号：WO2003022853A1

  公开（公告）日：2003-03-20

  The present invention relates to a method for the preparation of hexahydro-furo[2,3-b]furan-3-ol as well as novel intermediates for use in said method. More in particular the invention relates to a stereoselective method for the preparation of hexahydro-furo[2,3-b]furan-3-ol, and to a method amenable to industrial scaling up.

  本发明涉及一种制备六氢呋喃[2,3-b]呋喃-3-醇的方法，以及用于该方法的新型中间体。更具体地，本发明涉及一种立体选择性制备六氢呋喃[2,3-b]呋喃-3-醇的方法，以及一种适用于工业放大的方法。
• Method for the preparation of hexahydro-furo-[2,3-b]furan-3-ol
  申请人：——

  公开号：US20040249175A1

  公开（公告）日：2004-12-09

  The present invention relates to a method for the preparation of hexahydro-furo[2,3-b]furan-3-ol as well as novel intermediates for use in said method. More in particular the invention relates to a stereoselective method for the preparation of hexahydro-furo[2,3-b]furan-3-ol, and to a method amenable to industrial scaling up.

  本发明涉及一种制备六氢呋喃［2,3-b］呋喃-3-醇及其在该方法中使用的新型中间体的方法。更具体地，本发明涉及一种立体选择性制备六氢呋喃［2,3-b］呋喃-3-醇的方法，以及一种适用于工业放大的方法。
• METHODS FOR THE PREPARATION OF (3R,3aS,6aR) HEXAHYDRO-FURO[2,3-b]FURAN-3-OL
  申请人：Quaedflieg Mario Peter Jan Leonard

  公开号：US20070208184A1

  公开（公告）日：2007-09-06

  The present invention relates to methods for the preparation of diastereomerically pure (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-ol as well as a novel intermediate, (3aR,4S,6aS)4-methoxy-tetrahydro-furo[3,4-b]furan-2-one for use in said methods. More in particular the invention relates to a stereoselective method for the preparation of diastereomerically pure (3R,3aS,6aR)hexahydro-furo[2,3-b]furan-3-ol, as well as methods for the crystallization of (3aR,4S,6aS)4-methoxy-tetrahydro-furo[3,4-b]furan-2-one and for the epimerization of (3aR,4R,6aS)4-methoxy-tetrahydro-furo[3,4-b]-furan-2-one to (3aR,4S,6aS)4-methoxy-tetrahydro-furo[3,4-b]furan-2-one.

  本发明涉及制备对映异构体纯度高的(3R,3aS,6aR)六氢呋喃[2,3-b]呋喃-3-醇的方法，以及一种新的中间体(3aR,4S,6aS)4-甲氧基四氢呋喃[3,4-b]呋喃-2-酮，用于上述方法。更具体地说，本发明涉及一种立体选择性方法，用于制备对映异构体纯度高的(3R,3aS,6aR)六氢呋喃[2,3-b]呋喃-3-醇，以及用于结晶(3aR,4S,6aS)4-甲氧基四氢呋喃[3,4-b]呋喃-2-酮和对(3aR,4R,6aS)4-甲氧基四氢呋喃[3,4-b]呋喃-2-酮进行外消旋反应以得到(3aR,4S,6aS)4-甲氧基四氢呋喃[3,4-b]呋喃-2-酮的方法。