4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite

Base Information

• Chemical Name: 4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite
• CAS No.: 171284-20-1
• Molecular Formula: C₂₁H₃₇N₂O₃P
• Molecular Weight: 396.51
• Mol file: 171284-20-1.mol

Synonyms:4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite

Chemical Property of 4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite

There total 2 articles about 4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite 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: 61.0%

4-acetoxybenzyl alcohol (6309-46-2) + bis(diisopropylamino)chlorophosphine (56183-63-2) → 4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite (171284-20-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1080/15257779508009491

Reference yield: 53.0%

diisopropylamine (108-18-9) + methyl 4-(hydroxymethyl)phenylacetate (155380-11-3) → 4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite (171284-20-1)

Guidance literature:

methyl 4-(hydroxymethyl)phenylacetate; With phosphorus trichloride; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

diisopropylamine; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00737

Reference yield: 89.0%

9-Fluorenylmethanol (24324-17-2) + 4-acetoxybenzyl N,N,N’,N’-tetraisopropylphosphoramidite (171284-20-1) → 4-[({[bis(propan-2-yl)amino](9H-fluoren-9-ylmethoxy)phosphanyl}oxy)methyl]phenyl acetate

Guidance literature:

With 1H-tetrazole; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1002/anie.201503094

upstream raw materials:

4-acetoxybenzyl alcohol

bis(diisopropylamino)chlorophosphine

diisopropylamine

methyl 4-(hydroxymethyl)phenylacetate

Downstream raw materials:

4-acetyloxybenzyl bis(3'-azido-3'-deoxythymidin-5-yl) phosphate

Refernces

• 1、 Weinschenk, Lina,Schols, Dominique,Balzarini, Jan,Meier, Chris. "Nucleoside Diphosphate Prodrugs: Nonsymmetric DiPPro-Nucleotides". . p. 6114 - 6130. Retrieved 2015.