(2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol | 220774-98-1

• 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: (2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol
• 英文别名: (2R,3S,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-3-methyl-6-phenylsulfanyl-2-(trityloxymethyl)oxane-3,4-diol
• CAS: 220774-98-1
• 化学式: C₃₈H₄₆O₅SSi
• 分子量: 642.932
• InChiKey: HWTDCXPGPSYCQN-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：

  (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
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3-yl ester 在 重铬酸吡啶 、 cerium(III) chloride 、 四丁基氟化铵 、 乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.25h， 生成 (2R,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-6-phenylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3,4-diol
  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.