(2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)-1-butanol | 502481-96-1

• 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: (2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)-1-butanol
• 英文别名: 4-O-benzyl-2,3-O-isopropylidene-D-erythritol；[(4S,5R)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]methanol
• CAS: 502481-96-1
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: QNSNKEJGTRCSBP-QWHCGFSZSA-N

物化性质

• 沸点：
  362.0±27.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)-1-butanol 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)butane
  参考文献：
  名称：

  Versicolactones A and B: total synthesis and structure revision

  摘要：

  To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The H-1 and C-13 NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.120
• 作为产物：
  描述：

  (2R,3S)-4-Acetoxy-1-(benzyloxy)-2,3-butanetriol 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 (2S,3R)-4-benzyloxy-2,3-(propane-2,2-dioxy)-1-butanol
  参考文献：
  名称：

  Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 3: Role of the length of alditol side chain

  摘要：

  Five homologs of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, bearing alditols of different length (1g-1k) were synthesized by a stereoselective beta-mannosylation of appropriately protected mannosyl sulfoxide (2) with five alditols (1g: C2, 1h: C3, 1i: C4, 1j: C5 and 1k: C7 units), and their potential in modulating Ca2+ signaling were evaluated. Homologs with alditols of more than 4 carbons (1i, 1j and 1k) were equally or more potent than the parent compound (1a) regardless of the length of the alditol chain. Whereas activities of two homologs with shorter chains (1g and 1h) decreased to a considerable extent. The results indicated that the length of the alditol side chain was a crucial determinant for the potent calcium signal modulating activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.079

文献信息

• Highly stereocontrolled access to a tetrahydroxy long chain base using anti-selective additions
  作者：Makoto Shimizu、Manabu Kawamoto、Yasuki Niwa

  DOI：10.1039/a902386k

  日期：——

  Complete diastereostereoselection was attained for the addition of acetylide and benzyloxymethyl anions to a chiral aldehyde and an imine derived from meso-tartaric acid, leading to a facile synthesis of (2S,3S,4R,5R,6Z)-2-amino-1,3,4,5-tetrahydroxyoctadecene as its pentaacetyl derivative in enantiomerically pure form.

  对乙炔和苄氧基甲基阴离子与来自酒石酸的手性醛和亚胺的加成实现了完全的非对映体选择性，从而方便地合成了其五乙酰衍生物—(2S,3S,4R,5R,6Z)-2-氨基-1,3,4,5-四羟基十八烯，以对映体纯净的形式。
• Synthesis of saccharides and related polyhydroxylated natural products. 1. Simple alditols
  作者：T. Katsuki、A. W. M. Lee、P. Ma、V. S. Martin、S. Masamune、K. B. Sharpless、D. Tuddenham、F. J. Walker

  DOI：10.1021/jo00346a051

  日期：1982.3
• Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol
  作者：Chwang Siek Pak、Eun Lee、Ge Hyeong Lee

  DOI：10.1021/jo00058a038

  日期：1993.3

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.