(2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol | 220774-88-9

• 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: (2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol
• 英文别名: TBDMS(-3)[Trt(-6)]Gal(b)-SPh；(2S,3R,4S,5S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-2-phenylsulfanyl-6-(trityloxymethyl)oxane-3,5-diol
• CAS: 220774-88-9
• 化学式: C₃₇H₄₄O₅SSi
• 分子量: 628.905
• InChiKey: JOGMOYGYSFQDRM-IXNRCNHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  (2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-diol 在 吡啶 、 4-二甲氨基吡啶 、 重铬酸吡啶 、 cerium(III) chloride 、 四丁基氟化铵 、 乙酸酐 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 41.25h， 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 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (2S,3R,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-phenylsulfanyl-6-trityloxymethyl-tetrahydro-pyran-3,5-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