3-deoxy-5,6-O-isopropylidene-2-O-methanesulfonyl-D-arabino-hexono-1,4-lactone | 107036-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-5,6-O-isopropylidene-2-O-methanesulfonyl-D-arabino-hexono-1,4-lactone
• 英文别名: 3-deoxy-5,6-O-isopropylidene-2-O-mesyl-D-arabino-hexono-1,4-lactone；[(3S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxooxolan-3-yl] methanesulfonate
• CAS: 107036-72-6
• 化学式: C₁₀H₁₆O₇S
• 分子量: 280.299
• InChiKey: SSPNCWSTAHYGAD-BIIVOSGPSA-N

物化性质

• 熔点：
  142-144 °C(Solv: methanol (67-56-1))
• 沸点：
  483.9±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-deoxy-5,6-O-isopropylidene-2-O-methanesulfonyl-D-arabino-hexono-1,4-lactone 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 18.5h， 生成 2-amino-2,3-dideoxy-D-ribo-hexono-1,4-lactone hydrochloride
  参考文献：
  名称：

  Vitamin C and isovitamin C derived chemistry. 2. Synthesis of some enantiomerically pure 4,5,6-trihydroxylated norleucines

  摘要：

  DOI：

  10.1021/jo00382a022
• 作为产物：
  描述：

  (2R,3S,5S)-2-[(acetyloxy)methyl]-6-oxotetrahydro-2H-pyran-3,5-diyl diacetate 在 吡啶 、 Amberlite IR-120 (H+) 、 硫酸 、 sodium methylate 、 magnesium sulfate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 3-deoxy-5,6-O-isopropylidene-2-O-methanesulfonyl-D-arabino-hexono-1,4-lactone
  参考文献：
  名称：

  改进的3-脱氧-d-阿拉伯糖基己内酯的制备和合成用途：有效地合成Leptosphaerin

  摘要：

  摘要d-葡萄糖基-1,5-内酯乙酰化并随后用三乙胺处理，得到2,4,6-三-O-乙酰基-d-赤型-己基-2-enono-1,5-内酯。在钯/碳存在下，后者的氢化反应产生了由葡糖酸内酯计算出的几乎定量的产率的2,4,6-三-O-乙酰基-3-脱氧-d-阿拉伯糖基己基-1,5-内酯（5）。在三乙胺的存在下，用铂在碳上催化氢化5，得到定量的2,4,6-三-O-乙酰基-3-脱氧-d-阿拉伯糖基己糖。5的脱乙酰基产生3-deoxy-d-阿拉伯-己基-1,4-内酯，将其转化为3-deoxy-5,6-6-O-异亚丙基-2-O-甲磺酰基-d-arabino-hexono-1， 4-内酯（10）。后者被转化为2-乙酰氨基-2,3-二脱氧-d-赤-己基-2-enono-1,4-内酯（Leptosphaerin）。当10在酸的存在下在水中煮沸时，

  DOI：

  10.1016/s0008-6215(99)00007-5

文献信息

• An Aldol Approach to the Total Synthesis of Pamamycin 621 A
  作者：Guo-Bao Ren、Yikang Wu

  DOI：10.1021/ol902290v

  日期：2009.12.17

  Pamamycin 621 A was synthesized through a convergent route, with the THF rings constructed from Evans aldols in the presence of the chiral auxiliaries without suffering racemization or elimination. The basic amino group was introduced at a late stage through reduction of an azido group with n-Bu3SnH, which also demonstrates for the first time the great potential of this largely forgotten reduction protocol in synthesis of multifunctional substrates.
• Facile access to some chiral building blocks. Synthesis of verbalactone and exophilin A
  作者：Jian-Zhong Wu、Jian Gao、Guo-Bao Ren、Zhi-Bin Zhen、Yihua Zhang、Yikang Wu

  DOI：10.1016/j.tet.2008.10.050

  日期：2009.1

  D-Glucono-1,5-lactone, all inexpensive carbohydrate, was elaborated into chiral building blocks readily applicable in synthesis via practical routes without involving any expensive reagents or tedious operations. Application Of Such chiral building blocks in total synthesis is then exemplified through construction of verbalactone and exophilin A. The latter compound has not been synthesized to date. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of all diastereomeric methyl 2,5-anhydro-3-deoxy-hexonates: precursors to C-2-deoxynucleosides and THF-templated γ- and δ-amino acids
  作者：Mark P. Watterson、Alison A. Edwards、John A. Leach、Martin D. Smith、Osamu Ichihara、George W.J. Fleet

  DOI：10.1016/s0040-4039(03)01416-3

  日期：2003.7

  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.
• WHITE, JAMES D.;BADGER, RODNEY A.;KIZAR, HOLLIS S. (III);PALLENBERG, ALEX+, TETRAHEDRON, 45,(1989) N1, C. 6631-6644
  作者：WHITE, JAMES D.、BADGER, RODNEY A.、KIZAR, HOLLIS S. (III)、PALLENBERG, ALEX+

  DOI：——

  日期：——
• Vitamin C and isovitamin C derived chemistry. 2. Synthesis of some enantiomerically pure 4,5,6-trihydroxylated norleucines
  作者：Jozef A. J. M. Vekemans、Ronald G. M. De Bruyn、Roberta C. H. M. Caris、Antonius J. P. M. Kokx、Jeroen J. H. G. Konings、Erik F. Godefroi、Gordon J. F. Chittenden

  DOI：10.1021/jo00382a022

  日期：1987.3