(3R,4S)-3,4-bis(benzyloxy)dihydrofuran-2(3H)-one | 150575-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4S)-3,4-bis(benzyloxy)dihydrofuran-2(3H)-one
• 英文别名: 2,3-di-O-benzyl-L-threono-1,4-lactone；2,3-di-O-benzyl-L-threonolactone；(3R,4S)-3,4-bis(phenylmethoxy)oxolan-2-one
• CAS: 150575-74-9
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: ZVRLDOHTRJCNJM-DLBZAZTESA-N

物化性质

• 沸点：
  468.2±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3,4-bis(benzyloxy)dihydrofuran-2(3H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以81%的产率得到1,4-di-O-benzyl-L-threitol
  参考文献：
  名称：

  Displacement reactions on 2,3,4,6-tetra-O-benzyl-1,5-di-O-sulfonyl-D-glucitols. Synthesis of (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran

  摘要：

  Treatment of the 1,5-dimesylate and 1,5-ditosylate of 2,3,4,6-tetra-O-benzyl-D-glucitol 1 with tetrabutylammonium acetate in acetonitrile leads, through nucleophilic attack by O-2 at C-5 and normal displacement at C-1, to 1-O-acetyl-2,5-anhydro-3,4,6-tri-O-benzyl-L-iditol. In contrast, the corresponding 1,5-ditriflate on similar treatment undergoes displacement at C-1 by attack of O-4 and elimination of triflic acid between C-4 and C-5 to afford (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran.

  DOI：

  10.1039/p19930001003
• 作为产物：
  描述：

  (2R,3R)-2,3-bis(benzyloxy)-1,4-butanedioic anhydride 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium tetrahydroborate 、 三氯异氰尿酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 20.0h， 生成 (3R,4S)-3,4-bis(benzyloxy)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  -1,5-内酰胺基和四氢吡唑并吡啶-5-羧酸酯的合成：β -D-葡糖醛酸糖苷酶和α -L-异丁烯酸酶的抑制剂

  摘要：

  已知的葡糖二酸-1,5-内酰胺8，非对映体及其9 - 11，和tetrahydrotetrazolopyridine -5-羧酸盐12 - 14合成为的潜在抑制剂的β -D-葡糖醛酸和α -L-iduronidases。已知2,3-二ø -苄基-4,6- ø -亚苄基- d -半乳糖（16）转化到d-galactaro-和L-altraro -1,5-内酰胺9和11通过在半乳糖-1,5-内酰胺21分十二步进行，总收率分别为13％和2％。从已知的酒石酸酐41开始的不同策略导致了D-葡萄糖醛-1,5-内酰胺8，D-半乳糖醛-1,5-内酰胺9，L-idaro-1,5-内酰胺10和L -altraro-1,5-lactam 11分十步，总收率为4-20％。酸酐41被转化为L-苏糖酸酯46。将46烯烃烯烃化为（E）-或（Z）-烯烃47或48然后进行试剂或底物控制的二羟基化，内酯化，叠氮化，还原和脱保护反应，形成内酰胺8

  DOI：

  10.1002/hlca.200690066

文献信息

• Stereoselective Synthesis of <i>C</i>,<i>C</i>-Glycosides from <i>exo</i>-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer
  作者：Damien Tardieu、Marine Desnoyers、Claire Laye、Damien Hazelard、Nicolas Kern、Philippe Compain

  DOI：10.1021/acs.orglett.9b02496

  日期：2019.9.20

  We describe herein a convenient strategy for the construction of C,C-glycoside building blocks via the intermediacy of tertiary pseudoanomeric radicals. Application of an iron-mediated hydrogen atom transfer/Michael–Giese coupling enables the anomeric quaternization of readily available exo-glycals with good to complete stereocontrol in the pyranose and furanose series. Carefully optimized conditions

  我们在本文中描述了通过叔假异构基团的中间体构建C，C-糖苷结构单元的方便策略。铁介导的氢原子转移/ Michael–Giese偶联的应用使得易得的外糖的异头季铵化反应能够很好地完成吡喃糖和呋喃糖系列的立体控制。精心优化的条件允许使用具有挑战性的易取代的三取代衍生物，使其易于进一步精制成稳定的新糖缀合物。还讨论了直接C-二糖合成的初步结果。
• Synthesis of a Threosyl-C-nucleoside Phosphonate
  作者：Peng Nie、Elisabetta Groaz、Piet Herdewijn

  DOI：10.1002/ejoc.201901200

  日期：2019.10.24

  A general synthetic route was developed for the preparation of the first example of a new series of modified C‐nucleoside phosphonate analogues bearing a l‐threose sugar moiety and pyrrolo[2,1‐f][1,2,4]triazin‐4‐amine as nucleobase.

  开发了一条通用的合成路线，以制备带有l-苏糖部分和吡咯并[2,1-f] [1,2,4]三嗪-4的一系列新的修饰的C-核苷膦酸酯类似物系列的第一个实例。胺为核碱基。
• Synthesis of 4-Membered Carbasugars by Way of Stereoselective SmI₂-Mediated Aldehyde–Alkene Cyclization
  作者：Pierre-Antoine Nocquet、Damien Hazelard、Guillaume Gruntz、Philippe Compain

  DOI：10.1021/jo400732a

  日期：2013.7.5

  A stereodivergent synthesis of the first examples of 4-membered carbasugars has been achieved from vitamin C by way of an efficient intramolecular SmI2-mediated aldehyde-alkene coupling. In this key step, cylobutanes with four contiguous asymmetric centers are generated with a high level of stereocontrol.
• Displacement reactions on 2,3,4,6-tetra-O-benzyl-1,5-di-O-sulfonyl-D-glucitols. Synthesis of (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran
  作者：Paul A. Fowler、Alan H. Haines、Richard J. K. Taylor、Ewan J. T. Chrystal、Michael B. Gravestock

  DOI：10.1039/p19930001003

  日期：——

  Treatment of the 1,5-dimesylate and 1,5-ditosylate of 2,3,4,6-tetra-O-benzyl-D-glucitol 1 with tetrabutylammonium acetate in acetonitrile leads, through nucleophilic attack by O-2 at C-5 and normal displacement at C-1, to 1-O-acetyl-2,5-anhydro-3,4,6-tri-O-benzyl-L-iditol. In contrast, the corresponding 1,5-ditriflate on similar treatment undergoes displacement at C-1 by attack of O-4 and elimination of triflic acid between C-4 and C-5 to afford (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran.
• Synthesis of Glycaro-1,5-lactams and Tetrahydrotetrazolopyridine-5-carboxylates: Inhibitors ofβ-D-Glucuronidase andα-L-Iduronidase
  作者：Jagadish Pabba、Brian P. Rempel、Stephen G. Withers、Andrea Vasella

  DOI：10.1002/hlca.200690066

  日期：2006.4

  The known glucaro-1,5-lactam 8, its diastereoisomers 9–11, and the tetrahydrotetrazolopyridine-5-carboxylates 12–14 were synthesised as potential inhibitors of β-D-glucuronidases and α-L-iduronidases. The known 2,3-di-O-benzyl-4,6-O-benzylidene-D-galactose (16) was transformed into the D-galactaro- and L-altraro-1,5-lactams 9 and 11via the galactono-1,5-lactam 21 in twelve steps and in an overall yield

  已知的葡糖二酸-1,5-内酰胺8，非对映体及其9 - 11，和tetrahydrotetrazolopyridine -5-羧酸盐12 - 14合成为的潜在抑制剂的β -D-葡糖醛酸和α -L-iduronidases。已知2,3-二ø -苄基-4,6- ø -亚苄基- d -半乳糖（16）转化到d-galactaro-和L-altraro -1,5-内酰胺9和11通过在半乳糖-1,5-内酰胺21分十二步进行，总收率分别为13％和2％。从已知的酒石酸酐41开始的不同策略导致了D-葡萄糖醛-1,5-内酰胺8，D-半乳糖醛-1,5-内酰胺9，L-idaro-1,5-内酰胺10和L -altraro-1,5-lactam 11分十步，总收率为4-20％。酸酐41被转化为L-苏糖酸酯46。将46烯烃烯烃化为（E）-或（Z）-烯烃47或48然后进行试剂或底物控制的二羟基化，内酯化，叠氮化，还原和脱保护反应，形成内酰胺8