4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester | 220775-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-3-methyl-6-phenylsulfanyloxan-4-yl] 4-oxopentanoate
• CAS: 220775-04-2
• 化学式: C₁₈H₂₄O₇S
• 分子量: 384.45
• InChiKey: VMNVQSVFUGWWNA-FXXCCUJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester 在 Jones-reagent 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以65%的产率得到phenyl 2-O-levulinoyl-4-C-methyl-1-thio-β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Expeditious route to F unit building block of moenomycin A

  摘要：

  Synthesis of the versatile F sugar unit building block of moenomycin A, Phenyl 2-O-levulinoyl-4-C-methyl-1-thio-beta-D-glucopyranosiduronic acid is described starting from phenyl 1-thio-beta-D-galactopyranoside. The key synthetic steps included: (I) Regioselective protection of the 3-OH group of phenyl 6-O-trityl-1-thio-beta-D-galactopyranoside as its TBDMS ether, (ii) TBAF mediated TBDMS group migration from the C-3 to C-2 position of phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-beta-D-galactopyranoside, and (iii) Selective deprotection of TBDMS and trityl groups in phenyl 2-O-levulinoyl-3-O-TBDMS-4-C-methyl-6-O-trityl-1 -thio-beta-D-glucopyranoside by DDQ. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)80003-8
• 作为产物：
  描述：

  (2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol 在 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 28.0h， 生成 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-3-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Expeditious route to F unit building block of moenomycin A

  摘要：

  Synthesis of the versatile F sugar unit building block of moenomycin A, Phenyl 2-O-levulinoyl-4-C-methyl-1-thio-beta-D-glucopyranosiduronic acid is described starting from phenyl 1-thio-beta-D-galactopyranoside. The key synthetic steps included: (I) Regioselective protection of the 3-OH group of phenyl 6-O-trityl-1-thio-beta-D-galactopyranoside as its TBDMS ether, (ii) TBAF mediated TBDMS group migration from the C-3 to C-2 position of phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-beta-D-galactopyranoside, and (iii) Selective deprotection of TBDMS and trityl groups in phenyl 2-O-levulinoyl-3-O-TBDMS-4-C-methyl-6-O-trityl-1 -thio-beta-D-glucopyranoside by DDQ. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)80003-8

文献信息

• Expeditious route to F unit building block of moenomycin A
  作者：Ramesh Kakarla、Manuka Ghosh、Jan A. Anderson、Richard G. Dulina、Michael J. Sofia

  DOI：10.1016/s0040-4039(98)80003-8

  日期：1999.1

  Synthesis of the versatile F sugar unit building block of moenomycin A, Phenyl 2-O-levulinoyl-4-C-methyl-1-thio-beta-D-glucopyranosiduronic acid is described starting from phenyl 1-thio-beta-D-galactopyranoside. The key synthetic steps included: (I) Regioselective protection of the 3-OH group of phenyl 6-O-trityl-1-thio-beta-D-galactopyranoside as its TBDMS ether, (ii) TBAF mediated TBDMS group migration from the C-3 to C-2 position of phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-beta-D-galactopyranoside, and (iii) Selective deprotection of TBDMS and trityl groups in phenyl 2-O-levulinoyl-3-O-TBDMS-4-C-methyl-6-O-trityl-1 -thio-beta-D-glucopyranoside by DDQ. (C) 1998 Elsevier Science Ltd. All rights reserved.