(2R,3R)-3-(4-methoxybenzyloxy)-butan-1,2,4-triol | 152386-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-3-(4-methoxybenzyloxy)-butan-1,2,4-triol
• 英文别名: (2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol；(2R,3R)-3-[(4-methoxyphenyl)methoxy]butane-1,2,4-triol
• CAS: 152386-84-0
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: PJXCABOWNRSIIN-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-(4-methoxybenzyloxy)-butan-1,2,4-triol 在 4-二甲氨基吡啶 、 草酰氯 、 硫酸 、 对甲苯磺酸 、 二甲基亚砜 、 苯基锂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.83h， 生成 (2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol
  参考文献：
  名称：

  从D-酒石酸对映体合成D-赤型-鞘氨醇

  摘要：

  描述了通过叠氮鞘氨醇（2）有效的对映体特异性合成D-赤型-鞘氨醇（1），绝对立体化学衍生自D-酒石酸。

  DOI：

  10.1016/s0040-4020(01)81834-2
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 在 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 对甲苯磺酸 、 lithium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、1.33 kPa 条件下， 反应 35.5h， 生成 (2R,3R)-3-(4-methoxybenzyloxy)-butan-1,2,4-triol
  参考文献：
  名称：

  从D-酒石酸对映体合成D-赤型-鞘氨醇

  摘要：

  描述了通过叠氮鞘氨醇（2）有效的对映体特异性合成D-赤型-鞘氨醇（1），绝对立体化学衍生自D-酒石酸。

  DOI：

  10.1016/s0040-4020(01)81834-2

文献信息

• Studies toward the Unique Pederin Family Member Psymberin: Full Structure Elucidation, Two Alternative Total Syntheses, and Analogs
  作者：Yu Feng、Xin Jiang、Jef K. De Brabander

  DOI：10.1021/ja3057612

  日期：2012.10.17

  Two synthetic approaches to psymberin have been accomplished. A highly convergent first generation synthesis led to the complete stereochemical assignment and demonstrated that psymberin and irciniastatin A are identical compounds. This synthesis featured a diastereoselective aldol coupling between the aryl fragment and a central tetrahydropyran core and a novel one-pot procedure to convert an amide, via intermediacy of a sensitive methyl imidate, to the N-acyl aminal reminiscent of psymberin. The highlights of the second generation synthesis include an efficient iridium-catalyzed enantioselective bisallylation of neopentyl glycol and a stepwise Sonogashira coupling/cycloisomerization/reduction sequence to construct the dihydroisocoumarin unit. The two synthetic avenues were achieved in 17-18 steps (longest linear sequence, similar to 14-15 isolations) from 3 fragments prepared in 7-8 (first generation) and 3-8 (second generation) steps each. This convergent approach allowed for the preparation of sufficient amounts of psymberin (similar to 0.5 g) for follow-up biological studies. Meanwhile, our highly flexible strategy enabled the design and synthesis of multiple analogs, including a psymberin pederin hybrid, termed psympederin, that proved crucial to a comprehensive understanding of the chemical biology of psymberin and related compounds that will be described in a subsequent manuscript.
• Namyslo, Jan-Christoph; Schaefer, Renate; Maier, Martin E., Journal fur Praktische Chemie (Weinheim), 1999, vol. 341, # 6, p. 557 - 561
  作者：Namyslo, Jan-Christoph、Schaefer, Renate、Maier, Martin E.

  DOI：——

  日期：——
• An enantiospecific synthesis of D-erythro-sphingosine from D-tartaric acid
  作者：Peter Somfai、Roger Olsson

  DOI：10.1016/s0040-4020(01)81834-2

  日期：1993.7

  An efficient enantiospecific synthesis of D-erythro-sphingosine (1) via azidosphingosine (2) is described, the absolute stereochemistry being derived from D-tartaric acid.

  描述了通过叠氮鞘氨醇（2）有效的对映体特异性合成D-赤型-鞘氨醇（1），绝对立体化学衍生自D-酒石酸。
• Synthesis and disproof of the structure proposed for the tetrahydrofuranol isolated from <i>Michelia compressa</i> var. <i>lanyuensis</i> (Magnoliaceae)
  作者：Yong-Qing Yang

  DOI：10.1080/14786419.2015.1129331

  日期：2016.7.17

  The previously proposed structure for a tetrahydrofuranol isolated from the leaves of Michelia compressa var. lanyuensis (Magnoliaceae) was synthesised in an enantiopure form using diethyl D-tartarate as the starting material. The synthetic sample showed spectroscopic data incompatible with those for the natural product and thus unequivocally disproved the previously assigned structure.[GRAPHICS].