(R)-3-benzyloxy-1-hydroxytetradecane | 139623-16-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-3-benzyloxy-1-hydroxytetradecane
• 英文别名: (R)-3-(Benzyloxy)tetradecan-1-ol；(R)-3-Benzyloxy-1-tetradecanol；(3R)-3-phenylmethoxytetradecan-1-ol
• CAS: 139623-16-8
• 化学式: C₂₁H₃₆O₂
• 分子量: 320.516
• InChiKey: BDNJHLQOWXQLQF-OAQYLSRUSA-N

物化性质

• 沸点：
  443.2±20.0 °C(Predicted)
• 密度：
  0.939±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3-benzyloxy-1-hydroxytetradecane 在 [C₈H₁₂Ir(PMePh₂)2]PF₆ 、 氢气 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of GLA-60 type pyran carboxylic acids with an alkyl chain instead of an ester chain as LPS-antagonists

  摘要：

  Synthesis of GLA-60 type pyran carboxylic acid analogues with an alkyl chain instead of an ester chain and their LPS-antagonist activity toward human U937 cells are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00055-6
• 作为产物：
  描述：

  Decylmagnesium bromide 在 二异丁基氢化铝 、 copper(I) bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R)-3-benzyloxy-1-hydroxytetradecane
  参考文献：
  名称：

  通过基于自由基环化的策略立体选择性合成（-）-四氢脂肪抑制素

  摘要：

  描述了一种用于全合成（-）-四氢脂肪抑制素的有效而灵活的方法。合成策略的主要特征是立体控制的自由基环化和成功利用市售的S-苹果酸。

  DOI：

  10.1016/j.tetlet.2006.04.101

文献信息

• Lipid-A analogs: monosaccharide and dissaccharide compounds for
  申请人：IGEN Incorporated

  公开号：US05593969A1

  公开（公告）日：1997-01-14

  A compound of the formula: ##STR1## wherein: each of R.sub.1, R.sub.1 ', R.sub.2 and R.sub.2 ' independent of each other is a substituted or unsubstituted, branched or linear C.sub.1-12 alkyl, alkene or alkyne group, R.sub.3 is OH, OCH.sub.3, CH.sub.2 COOH or ##STR2## wherein each of R.sub.2" and R.sub.2 '41 independent of each other is a substituted or unsubstituted, branched or linear C.sub.1-12 alkyl, alkene or alkyne group and: A=NH.sub.2, X=P(OH), Y=Z=C, B=OCH.sub.3, or A=OH, X=P(OH), X=Z=C, B (if present)=OCH.sub.3, or A=OCO(CH.sub.2).sub.n NH.sub.2, X=P(OH), Y=Z=C, B=OCH.sub.3, wherein n=1-10, or A=OH, X=P(OH), Y=Z=C, B=O(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-10, or A=OH, X=P(OH), Y=Z=C, B=(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-10, or A=NH.sub.2, X=Z=C, Y=P(OH), B=OCH.sub.3, or A=OH, X=Z=C, Y=P(OH), B (if present)=OCH.sub.3, or A=OCO(CH.sub.2).sub.n NH.sub.2, X=Z=C, Y=P(OH), B=OCH.sub.3, wherein n=1-10, or A=OH, X=Z=C, Y=P(OH), B=O(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-10, or A=OH, X=Z=C, Y=P(OH), B=(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-11, or A=NH.sub.2, X=Y=C, Z=P(OH), B=OCH.sub.3, or A=OH, X=Y=C, Z=P(OH), B (if present)=OCH.sub.3, or A=OCO(CH.sub.2).sub.n NH.sub.2, X=Y=C, Z=P(OH), B=OCH.sub.3, wherein n=1-10, or A=OH, X=Y=C, Z=P(OH), B=O(CH.sub.2).sub.n CO.sub.2 H, wherein n=1-10, or A=OH, X=Y=C, Z=P (OH), B=(CH.sub.2).sub.n CO.sub.2 H and n=1-11 is disclosed. The compounds may be use to inhibit binding of Lipid A to Lipid A receptors.

  该化合物的公式为：##STR1## 其中：每个R.sub.1，R.sub.1'，R.sub.2和R.sub.2'彼此独立，是取代或未取代的支链或直链C.sub.1-12烷基，烯基或炔基，R.sub.3为OH，OCH.sub.3，CH.sub.2COOH或##STR2## 其中R.sub.2"和R.sub.2'41彼此独立，是取代或未取代的支链或直链C.sub.1-12烷基，烯基或炔基，且：A=NH.sub.2，X=P(OH)，Y=Z=C，B=OCH.sub.3，或A=OH，X=P(OH)，X=Z=C，B（如果存在）=OCH.sub.3，或A=OCO(CH.sub.2).sub.nNH.sub.2，X=P(OH)，Y=Z=C，B=OCH.sub.3，其中n=1-10，或A=OH，X=P(OH)，Y=Z=C，B=O(CH.sub.2).sub.nCO.sub.2H，其中n=1-10，或A=OH，X=P(OH)，Y=Z=C，B=(CH.sub.2).sub.nCO.sub.2H，其中n=1-10，或A=NH.sub.2，X=Z=C，Y=P(OH)，B=OCH.sub.3，或A=OH，X=Z=C，Y=P(OH)，B（如果存在）=OCH.sub.3，或A=OCO(CH.sub.2).sub.nNH.sub.2，X=Z=C，Y=P(OH)，B=OCH.sub.3，其中n=1-10，或A=OH，X=Z=C，Y=P(OH)，B=O(CH.sub.2).sub.nCO.sub.2H，其中n=1-10，或A=OH，X=Z=C，Y=P(OH)，B=(CH.sub.2).sub.nCO.sub.2H，其中n=1-11，或A=NH.sub.2，X=Y=C，Z=P(OH)，B=OCH.sub.3，或A=OH，X=Y=C，Z=P(OH)，B（如果存在）=OCH.sub.3，或A=OCO(CH.sub.2).sub.nNH.sub.2，X=Y=C，Z=P(OH)，B=OCH.sub.3，其中n=1-10，或A=OH，X=Y=C，Z=P(OH)，B=O(CH.sub.2).sub.nCO.sub.2H，其中n=1-10，或A=OH，X=Y=C，Z=P(OH)，B=(CH.sub.2).sub.nCO.sub.2H，其中n=1-11。这些化合物可用于抑制脂质A与脂质A受体的结合。
• Lipid-A analogs: new monosaccharide and disaccharide intermediates for
  申请人：Igen, Inc.

  公开号：US05597573A1

  公开（公告）日：1997-01-28

  The present invention relates to novel amidine components of formula (II): ##STR1## A method for eliciting antibodies in an animal which bind to Lipid A or LPS comprising administering to the animal as an immunogen a composition comprising such a compound is also disclosed.

  本发明涉及式（II）的新型酰胺组分：##STR1## 还公开了一种通过向动物注射包含这种化合物的组合物作为免疫原来诱导动物产生与脂质A或LPS结合的抗体的方法。
• Total synthesis of (-)-tetrahydrolipstatin
  作者：Stephen Hanessian、Ashok Tehim、Ping Chen

  DOI：10.1021/jo00079a022

  日期：1993.12

  The total synthesis of (-)-tetrahydrolipstatin utilizing two approaches is described. In the first, L-malic acid was used as a chiral template to obtain enantiomerically pure (R)-3-(benzyloxy)-tetradecanal (11) which was chain-extended using 1-(trimethylsilyl)-2-nonene and a Lewis acid. This advanced intermediate was further elaborated to the target compound in good overall yield. The second approach utilized lauraldehyde as a starting material and capitalizes on an asymmetric allylboronation (91 % ee). The product could be obtained enantiomerically pure by conversion to the (R)-acetoxymandelate ester and hydrolysis. Oxidative cleavage of the terminal double bond led to 11 which was further extended using 1,3- and 1,2-asymmetric induction based on existing neighboring chirality. The synthesis of tetrahydrolipstatin using the second approach comprises seven steps from 11 and proceeds in 38 % overall yield.
• Synthesis of 2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-3-O-[(3R)-3-hydroxytetradecanyl]-α-d-glucopyranosyl dihydrogen phosphate and 2-deoxy-2-[(3R)-3-hydroxy-tetradecanamido]-3-O-[3R)-3-hydroxytetradecanyl]-4-O-phosphono-d-glucopyranose
  作者：Masao Shiozaki、Yoshiyuki Kobayashi、Noboru Ishida、Masami Arai、Tetsuo Hiraoka、Masahiro Nishijima、Sayuri Kuge、Toshiaki Otsuka、Yuzuru Akamatsu

  DOI：10.1016/0008-6215(91)89006-2

  日期：1991.12

  Both a 3-O-alkyl lipid X analogue and its 4-O-phosphono isomer were synthesized from allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.
• LIPID-A ANALOGS: NEW MONOSACCHARIDE AND DISACCHARIDE INTERMEDIATES FOR ELICITING THERAPEUTIC ANTIBODIES AND FOR ANTITUMOR AND ANTIVIRAL ACTIVITIES
  申请人：IGEN, INC.

  公开号：EP0639977A1

  公开（公告）日：1995-03-01