(3S,4R,5R,6R)-6-Benzyloxymethyl-3,4-dihydroxy-5-methyl-tetrahydro-pyran-2-one | 212767-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5R,6R)-6-Benzyloxymethyl-3,4-dihydroxy-5-methyl-tetrahydro-pyran-2-one
• CAS: 212767-79-8
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: CNNRVRIIVNDJHK-SYEHKZFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6R)-6-Benzyloxymethyl-3,4-dihydroxy-5-methyl-tetrahydro-pyran-2-one 在 palladium on activated charcoal 咪唑 、 swern reagent 、 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,4S,4aR,9aS)-6,6,8,8-Tetraisopropyl-4-methyl-1-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-3-carbaldehyde
  参考文献：
  名称：

  Synthesis and biological activity of lactones en route to Altohyrtin A

  摘要：

  Lactones 2 and 7 were synthesised and tested against six human tumour cell lines (Pancrens-a, BXPC-3), (Thyroid ca, KAT-4), (Thyroid ca, SW1736), (Lung-NSC, NCI-H460), (Pharynx-sq, FADU) and (Prostate, DU-145). Lactone 7 proved inactive, but lactone 2 displayed some activity against four of the six cell lines examined. Both lactones were converted into an intermediate 5 en route to Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00268-6
• 作为产物：
  描述：

  (2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到(3S,4R,5R,6R)-6-Benzyloxymethyl-3,4-dihydroxy-5-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Synthesis and biological activity of lactones en route to Altohyrtin A

  摘要：

  Lactones 2 and 7 were synthesised and tested against six human tumour cell lines (Pancrens-a, BXPC-3), (Thyroid ca, KAT-4), (Thyroid ca, SW1736), (Lung-NSC, NCI-H460), (Pharynx-sq, FADU) and (Prostate, DU-145). Lactone 7 proved inactive, but lactone 2 displayed some activity against four of the six cell lines examined. Both lactones were converted into an intermediate 5 en route to Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00268-6

文献信息

• An efficient protocol for the stereoselective dihydroxylation of ene-ester systems
  作者：Stephen A. Hermitage、Alison Murphy、Poul Nielsen、Stanley M. Roberts

  DOI：10.1016/s0040-4020(98)00800-x

  日期：1998.10

  Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO4 and NMO conditions using the intrinsic diastereoselectivity in alpha-methyl beta-OTBS systems. This intrinsic diastereoselection can be reversed using 'super' AD-mix to give the opposite diastereomer also in good selectivity. The regioselection of dihydroxylation in diene esters using a modified 'super' AD-mix was poor. This methodology can be applied towards the synthesis of part structures of the marine macrolide Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.