phenacyl (2S,17S,18S,22R)-2,17,18-triacetyloxy-22-[(2S,3R,4S,5R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]oxyhexacosanoate | 112848-51-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenacyl (2S,17S,18S,22R)-2,17,18-triacetyloxy-22-[(2S,3R,4S,5R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]oxyhexacosanoate
• CAS: 112848-51-8；112924-83-1
• 化学式: C₇₂H₁₀₆O₃₁
• 分子量: 1467.62
• InChiKey: PVFWIUDLOOUWTP-DPKWXMTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  103
• 可旋转键数：
  57
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  388
• 氢给体数：
  0
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  phenacyl (2S,17S,18S,22R)-2,17,18-triacetyloxy-22-[(2S,3R,4S,5R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]oxyhexacosanoate 生成 (2S,17S,18S)-2,17,18-Trimethoxy-22-oxo-hexacosanoic acid methyl ester
  参考文献：
  名称：

  Structures of deacetyl glykenins-a, b, and c, glycosidic antibiotics from

  摘要：

  DOI：

  10.1016/s0040-4039(00)80739-x
• 作为产物：
  描述：

  Deactylglykenin C 、 2-溴苯乙酮 、 乙酸酐 、 吡啶 生成 phenacyl (2S,17S,18S,22R)-2,17,18-triacetyloxy-22-[(2S,3R,4S,5R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R)-4,5-diacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]oxyhexacosanoate
  参考文献：
  名称：

  NISHIDA, FUMIKO;MORJ, YUJI;SONOBE, CHIHARU;SUZUKI, MAKOTO;MEEVOOTISOM, VI+, J. ANTIBIOTICS, 44,(1991) N, C. 541-545

  摘要：

  DOI：

文献信息

• Structure elucidation of glycosidic antibiotics, glykenins, from Basidiomycetes sp. II. Absolute structures of unusual polyhydroxylated C26-fatty acids, aglycones of glykenins.
  作者：Fumiko NISHIDA、Yuji MORI、Naoko ROKKAKU、Sayuri ISOBE、Takeyuki FURUSE、Makoto SUZUKI、Vithaya MEEVOOTISOM、Timothy W. FLEGEL、Yodhathai THEBTARANONTH、Suthum INTARARUANGSORN

  DOI：10.1248/cpb.38.2381

  日期：——

  The structures of three aglycones of glykenins, produced by Basidiomycetes sp., were determined to be (2S, 16R, 17S, 21R)-2, 16, 17, 21-, (2S, 17R, 18S, 22R)-2, 17, 18, 22-, and (2S, 17S, 18S, 22R)-2, 17, 18, 22-tetrahydroxyhexacosanoic acids (3a-c). The absolute configurations of two of the four hydroxy groups in 3a-c were established by chiral synthesis of the degradation products (6a-c and 7a-c). Chemical transformation of 3a-c to 6, 8-dioxabicyclo[3.2.1]octane derivatives (18-c) revealed the relative and absolute configurations of the acyclic 1, 2-diol moieties in 3a-c.

  巴斯德霉菌属（Basidiomycetes sp.）产生的甘草甜素的三种缩醛的结构被确定为（2S, 16R, 17S, 21R）-2, 16, 17, 21-、（2S, 17R, 18S, 22R）-2, 17, 18, 22-和（2S, 17S, 18S, 22R）-2, 17, 18, 22-四羟基六二十酸（3a-c）。通过手性合成降解产物（6a-c 和 7a-c），确定了 3a-c 中四个羟基中两个羟基的绝对构型。将 3a-c 化学转化为 6，8-二氧双环[3.2.1]辛烷衍生物 (18-c) 揭示了 3a-c 中无环状 1，2-二醇分子的相对和绝对构型。
• NISHIDA, FUMIKO;MORI, YUJI;ROKKAKU, NAOKO;ISOBE, SAYURI;FURUSE, TAKEYUKI;+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 2381-2389
  作者：NISHIDA, FUMIKO、MORI, YUJI、ROKKAKU, NAOKO、ISOBE, SAYURI、FURUSE, TAKEYUKI、+

  DOI：——

  日期：——
• NISHIDA, FUMIKO;MORJ, YUJI;SONOBE, CHIHARU;SUZUKI, MAKOTO;MEEVOOTISOM, VI+, J. ANTIBIOTICS, 44,(1991) N, C. 541-545
  作者：NISHIDA, FUMIKO、MORJ, YUJI、SONOBE, CHIHARU、SUZUKI, MAKOTO、MEEVOOTISOM, VI+

  DOI：——

  日期：——
• NISHIDA, FUMIKO;MORI, YUJI;ISOBE, SAYURI;FURUSE, TAKEYUKI;SUZUKI, MAKOTO;+, TETRAHEDRON LETT., 29,(1988) N 41, C. 5287-5290
  作者：NISHIDA, FUMIKO、MORI, YUJI、ISOBE, SAYURI、FURUSE, TAKEYUKI、SUZUKI, MAKOTO、+

  DOI：——

  日期：——
• Structures of deacetyl glykenins-a, b, and c, glycosidic antibiotics from
  作者：Fumiko Nishida、Yuji Mori、Sayuri Isobe、Takeyuki Furuse、Makoto Suzuki、Vithaya Meevootisom、Timothy W. Flegel、Yodhathai Thebtaranonth

  DOI：10.1016/s0040-4039(00)80739-x

  日期：1988.1