1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione

Base Information

• Chemical Name: 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione
• CAS No.: 95694-62-5
• Molecular Formula: C₃₅H₄₇N₃O₆SSi
• Molecular Weight: 665.926
• Mol file: 95694-62-5.mol

Synonyms:1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione

Chemical Property of 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione

There total 2 articles about 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione 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: 16.2%

tert-butyldimethylsilyl chloride (18162-48-6) + syn-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (minor diastereomer) (95782-44-8) → 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-<((tert-butyldimethylsilyl)oxy)methyl>-3''-(hydroxypropyl)>-2,5-piperazinedione (95694-63-6) + 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione (95694-62-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 14h; Ambient temperature;

DOI:10.1021/ja00297a035

Reference yield:

1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-(2-γ-butyrolactonyl)-2,5-piperazinedione (syn, minor diastereomer) (92216-26-7) → 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione (95694-62-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 19 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

2: 35 percent / Et₃N / tetrahydrofuran / 14 h / Ambient temperature

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran;

DOI:10.1021/ja00297a035

Reference yield: 75.0%

methanesulfonyl chloride (124-63-0) + 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione (95694-62-5) → 1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-<((methylsulfonyl)oxy)methyl>-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione (95782-35-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 0.583333h; Ambient temperature;

DOI:10.1021/ja00297a035

upstream raw materials:

tert-butyldimethylsilyl chloride

syn-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (minor diastereomer)

1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-(2-γ-butyrolactonyl)-2,5-piperazinedione (syn, minor diastereomer)

Downstream raw materials:

1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-<((methylsulfonyl)oxy)methyl>-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione

8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-2-oxabicyclo<4.2.2>decane-7,9-dione

(1S,6R)-6-hydroxy-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione

8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione