Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester

Base Information

• Chemical Name: Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester
• CAS No.: 162792-24-7
• Molecular Formula: C₄₇H₅₆NO₆P
• Molecular Weight: 761.938
• Mol file: 162792-24-7.mol

Synonyms:Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester

Chemical Property of Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester

There total 14 articles about Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite (108549-21-9) + 1D-2,4,5,6-tetra-O-benzyl-3-deoxy-myo-inositol (162792-23-6) → Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester (162792-24-7)

Guidance literature:

With N,N-diisopropylamine tetrazolide; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(97)10003-5

Reference yield:

(1R,2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-methoxymethoxy-cyclohexanol (162792-21-4) → Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester (162792-24-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / NaH, Bu₄NI / dimethylformamide / Ambient temperature

2: 77 percent / conc. HCl / methanol / 2 h / Heating

3: 100 percent / diisopropylammonium tetrazolide / CH₂Cl₂ / 24 h / Ambient temperature

With hydrogenchloride; N,N-diisopropylamine tetrazolide; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10003-5

Reference yield:

C36H40O6 (162792-22-5) → Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester (162792-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / conc. HCl / methanol / 2 h / Heating

2: 100 percent / diisopropylammonium tetrazolide / CH₂Cl₂ / 24 h / Ambient temperature

With hydrogenchloride; N,N-diisopropylamine tetrazolide; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(97)10003-5

upstream raw materials:

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite

1D-2,4,5,6-tetra-O-benzyl-3-deoxy-myo-inositol

(benzyloxy)chloro(diisopropylamino)phosphane

benzyl bromide

Downstream raw materials:

1D-3-deoxyphosphatidylinositol

Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester

Phosphoric acid benzyl ester (R)-2-methoxy-3-octadecyloxy-propyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester

3-deoxy PI ether lipid

Refernces

• 1、 Andresen, Thomas L.,Skytte, Dorthe M.,Madsen, Robert. "Synthesis of anti-tumour phosphatidylinositol analogues from glucose by the use of ring-closing olefin metathesis". . p. 2951 - 2957. Retrieved 2007/10/03.
• 2、 Qiao,Nan,Kunkel,Gallegos,Powis,Kozikowski. "3-Deoxyl-D-myo-inositol 1-phosphate, 1-phosphate, and ether lipid analogues as inhibitors of phosphatidylinositol-3-kinase signaling and cancer cell growth". . p. 3303 - 3306. Retrieved 2007/10/03.