tribenzyl methyl methylenebis(phosphonate) | 166049-85-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: tribenzyl methyl methylenebis(phosphonate)
• 英文别名: methylenebisphosphonic acid tribenzyl methyl ester；[Bis(phenylmethoxy)phosphorylmethyl-methoxyphosphoryl]oxymethylbenzene
• CAS: 166049-85-0
• 化学式: C₂₃H₂₆O₆P₂
• 分子量: 460.403
• InChiKey: NDADWTBAEYPZBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tribenzyl methyl methylenebis(phosphonate) 在 sodium hydride 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以72%的产率得到difluoromethylenebisphosphonic acid tribenzyl methyl ester
  参考文献：
  名称：

  Synthesis of Stable Analogues of Thiamine Di- and Triphosphate as Tools for Probing a New Phosphorylation Pathway

  摘要：

  Thiamine (vitamin B1) is an essential nutritional factor metabolized inside the body in its mono-, di-, and triphosphate forms. Although the action of thiamine and thiamine diphosphate have been intensely investigated, many questions remain unanswered and the role of thiamine triphosphate is still especially unknown. To probe recent hypotheses on the implication of thiamine triphosphate in a new phosphorylation pathway involving synaptic proteins, we synthesized a series of thiamine di- and triphosphate analogues that are resistant to both enzymatic and chemical hydrolyses. The key step in the preparation of the title compounds is the coupling of thiamine propyl disulfide with adequately protected methylenebisphosphonic acid, the corresponding triphosphate analogue, and difluoromethylenebisphosphonic acid.

  DOI：

  10.1002/1521-3765(20021018)8:20<4649::aid-chem4649>3.0.co;2-m
• 作为产物：
  描述：

  dibenzyl (chloromethyl)phosphonate 、 Phosphorous acid dibenzyl ester methyl ester 140.0 ℃ 、2.0 kPa 条件下， 反应 8.0h， 以65%的产率得到tribenzyl methyl methylenebis(phosphonate)
  参考文献：
  名称：

  亚磷酸苄基酯在Michaelis-Arbuzov反应合成单，二和三磷酸酯类似物中的首次使用

  摘要：

  亚甲基苄基酯用于Micaelis-Arbuzov反应。特殊的实验条件允许制备一组单磷酸，二磷酸和三磷酸的膦酸酯类似物。此外，在非常温和的条件下以高收率除去所有膦酸酯苄酯基团之后，区域选择性单脱保护使这些分子成为合成具有生物学意义的多磷酸化化合物（例如核苷酸）的类似物的有用组成部分。

  DOI：

  10.1002/hlca.19950780314

文献信息

• Synthesis of Di- and Triphosphate Ester Analogs via a Modified Michaelis-Arbuzov Reaction
  作者：M Saady

  DOI：10.1016/00404-0399(50)10097-

  日期：1995.7.17
• COMPOSITIONS AND METHODS OF MODULATING THE IMMUNE RESPONSE BY ACTIVATING ALPHA PROTEIN KINASE 1
  申请人：Shanghai Yao Yuan Biotechnology Co., Ltd.

  公开号：US20220017560A1

  公开（公告）日：2022-01-20

  The disclosure provides compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A 1 , A 2 , L 1 , L 2 , L 3 , Z 1 , Z 2 , W 1 , W 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined herein.
• [EN] DIPHOSPHATE OR TRIPHOSPHATE NON-HYDROLYSABLE STABLE ANALOGUES AND METHODS FOR THEIR PREPARATION<br/>[FR] ANALOGUES STABLES, NON HYDROLYSABLES, DE DIPHOSPHATES OU TRIPHOSPHATES ET LEURS PROCEDES DE PREPARATION
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：WO1996000733A1

  公开（公告）日：1996-01-11

  (EN) Diphosphate or triphosphate non-hydrolysable stable analogues and methods for their preparation. These analogues are of formula (I) in which R1, R2, R3, R4 and R5 are a hydrocarbon group, an aryl group, a quaternary ammonium group or a metal ion, R5 can also be a nucleoside derivative, X1 and X2 are CH2, CHF, CF2, CC12, CHC1 or NR6 and n=0 or 1. The analogues of the invention are for pharmaceutical, biological and therapeutical use.(FR) L'invention concerne des analogues stables, non hydrolysables, de diphosphates ou triphosphates et leurs procédés de préparation. Ces analogues répondent à la formule (I) dans laquelle R1, R2, R3, R4 et R5 sont un groupe hydrocarboné, un groupe aryle, un groupe ammonium quaternaire ou un ion métallique, R5 pouvant représenter de plus un dérivé de nucléoside, X1 et X2 sont CH2, CHF, CF2, CC12, CHC1 ou NR6 et n=0 ou 1. Ces analogues sont utilisables en pharmacie, en biologie et pour des suivis thérapeutiques.
• First Use of Benzyl Phosphites in theMichaelis-Arbuzov Reaction synthesis of mono-, Di-, and triphosphate analogs
  作者：Mourad Saady、Luc Lebeau、Charles Mioskowski

  DOI：10.1002/hlca.19950780314

  日期：1995.5.10

  Micaelis-Arbuzov reaction. Special experimental conditions allowed preparation of a set of phosphonate analogs of mono-, di-, and triphosphate. Furthermore, regioselective monodeprotection makes these molecules useful building blocks for the synthesis of analogs of polyphosphorylated compounds of biological interest (e.g. nucleotides), after removal of all phosphonate benzyl ester groups under very

  亚甲基苄基酯用于Micaelis-Arbuzov反应。特殊的实验条件允许制备一组单磷酸，二磷酸和三磷酸的膦酸酯类似物。此外，在非常温和的条件下以高收率除去所有膦酸酯苄酯基团之后，区域选择性单脱保护使这些分子成为合成具有生物学意义的多磷酸化化合物（例如核苷酸）的类似物的有用组成部分。
• Synthesis of Stable Analogues of Thiamine Di- and Triphosphate as Tools for Probing a New Phosphorylation Pathway
  作者：Emmanuel Klein、Hoàng-Oanh Nghiêm、Alain Valleix、Charles Mioskowski、Luc Lebeau

  DOI：10.1002/1521-3765(20021018)8:20<4649::aid-chem4649>3.0.co;2-m

  日期：2002.10.18

  Thiamine (vitamin B1) is an essential nutritional factor metabolized inside the body in its mono-, di-, and triphosphate forms. Although the action of thiamine and thiamine diphosphate have been intensely investigated, many questions remain unanswered and the role of thiamine triphosphate is still especially unknown. To probe recent hypotheses on the implication of thiamine triphosphate in a new phosphorylation pathway involving synaptic proteins, we synthesized a series of thiamine di- and triphosphate analogues that are resistant to both enzymatic and chemical hydrolyses. The key step in the preparation of the title compounds is the coupling of thiamine propyl disulfide with adequately protected methylenebisphosphonic acid, the corresponding triphosphate analogue, and difluoromethylenebisphosphonic acid.