phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-glucopyranoside | 220774-94-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3R,4R,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-3-methyl-6-phenylsulfanyl-2-(trityloxymethyl)oxane-3,5-diol
• CAS: 220774-94-7
• 化学式: C₃₈H₄₆O₅SSi
• 分子量: 642.932
• InChiKey: FEILIBJSFMROKS-YTCSVRQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.01
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 4-Oxo-pentanoic acid (2R,3R,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-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
• 作为产物：
  描述：

  苯基-1-硫醇-beta-D-半乳糖苷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 重铬酸吡啶 、 cerium(III) chloride 、 乙酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 25.0h， 生成 phenyl 3-O-TBDMS-4-C-methyl-6-O-trityl-1-thio-β-D-glucopyranoside
  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

• Diastereofacial selection in the 1,2-addition of MeMgX and McLi to 4-oxo sugar:Efficient synthesis of 4-C-methyl-l-S-β-D-gluco- and galactopyranoside building blocks of moenomycin
  作者：Manuka Ghosh、Ramesh Kakarla、Michael J. Sofia

  DOI：10.1016/s0040-4039(99)00823-0

  日期：1999.6

  The stereochemical course of the 1,2-addition upon treatment of various 1-thio-4-oxo sugars with MeMgX and MeLi has been determined. The effects of reagent, solvent, and neighboring functionalities in the gluco/galacto (non-chelation/chelation controlled) product distribution are detailed. Stereocontrolled 1,2-addition to these 4-oxo sugars provide access to a number of differently functionalized F unit building blocks of the moenomycin family, and demonstrate the versatility of this transformation. (C) 1999 Elsevier Science Ltd. All rights reserved.
• 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.