<2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus

Base Information

• Chemical Name: <2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus
• CAS No.: 145484-36-2
• Molecular Formula: C₃₁H₄₂NO₅P
• Molecular Weight: 539.652
• Mol file: 145484-36-2.mol

Synonyms:<2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus

Chemical Property of <2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus

There total 12 articles about <2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus 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: 90.7%

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite (108549-21-9) + (R)-2-(benzyloxy)-3-[(4-methoxybenzyl)oxy]propan-1-ol (145454-62-2) → <2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus (145484-36-2)

Guidance literature:

With 1H-tetrazole; In 1,2-dichloro-ethane; acetonitrile; at 0 ℃;

DOI:10.1246/bcsj.65.2643

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → <2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus (145484-36-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / (1S)-10-camphorsulfonic acid / tetrahydrofuran / 2.5 h / Heating

2: 1.) Zn(BH₄)2, 2.) TMSCl, 3.) imidazole

3: 93.8 percent / Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

4: 90.7 percent / 1H-tetrazole / 1,2-dichloro-ethane; acetonitrile / 0 °C

With 1H-imidazole; 1H-tetrazole; chloro-trimethyl-silane; zinc(II) tetrahydroborate; tetrabutyl ammonium fluoride; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1246/bcsj.65.2643

Reference yield:

(R)-3-(4-methoxybenzyloxy)propane-1,2-diol (109786-74-5) → <2-O-benzyl-3-O-(p-methoxybenzyl)-sn-glycero(1)>benzyloxo(diisopropylamido)phosphorus (145484-36-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / (1S)-10-camphorsulfonic acid / tetrahydrofuran / 2.5 h / Heating

2: 1.) Zn(BH₄)2, 2.) TMSCl, 3.) imidazole

3: 93.8 percent / Bu₄NF / tetrahydrofuran / 0.5 h / Ambient temperature

4: 90.7 percent / 1H-tetrazole / 1,2-dichloro-ethane; acetonitrile / 0 °C

With 1H-imidazole; 1H-tetrazole; chloro-trimethyl-silane; zinc(II) tetrahydroborate; tetrabutyl ammonium fluoride; [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1246/bcsj.65.2643

upstream raw materials:

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

(R)-2-(benzyloxy)-3-[(4-methoxybenzyl)oxy]propan-1-ol

benzaldehyde dimethyl acetal

(R)-3-(4-methoxybenzyloxy)propane-1,2-diol

Refernces