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

Base Information

• Chemical Name: syn-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (major diastereomer)
• CAS No.: 92098-03-8
• Molecular Formula: C₂₉H₃₃N₃O₆S
• Molecular Weight: 551.664
• Mol file: 92098-03-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about syn-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (major diastereomer) 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: 40.0%

1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-(2-γ-butyrolactonyl)-2,5-piperazinedione (syn, major diastereomer) (92098-11-8) → syn-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (major diastereomer) (92098-03-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; 2.) room temp., 1 h;

DOI:10.1021/ja00297a035

Reference yield:

syn-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (major diastereomer) (92098-03-8) → 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-(hydroxymethyl)-2-oxabicyclo<4.2.2>decane-7,9-dione (92098-12-9) + 7,9-bis(p-methoxybenzyl)-7,9-diaza-4-<(2'-hydroxyethyl)>-2-oxabicyclo<3.2.2>nonane-6,8-dione (95739-48-3)

Guidance literature:

With silver trifluoromethanesulfonate; In tetrahydrofuran; at 25 ℃; for 0.25h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00297a035

Reference yield:

syn-1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-(hydroxypropyl)>-2,5-piperazinedione (major diastereomer) (92098-03-8) → N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin (92098-17-4)

Guidance literature:

Multi-step reaction with 6 steps

1: AgOTf / tetrahydrofuran / 0.25 h / 25 °C

2: Et₃N / tetrahydrofuran / 12 h / Ambient temperature

3: NaBH₄ / ethanol / 0.33 h / 45 °C

4: 95.5 percent / 30percent H₂O₂ / tetrahydrofuran / 0.33 h / Heating

5: 1.) HMPA, n-butyllithium; 2.) O₂ / 1.) THF, -78 deg C, 7 min; 2.) THF, -78 deg C, 10 min, then --> room temp., 3 min

6: 1.) n-BuLi / 1.) THF, -98 deg C, 3 min; 2.) -98 deg C, 10 min, then --> room temp.

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; dihydrogen peroxide; oxygen; silver trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1021/ja00297a035

upstream raw materials:

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

Downstream raw materials:

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

7,9-bis(p-methoxybenzyl)-7,9-diaza-4-<(2'-hydroxyethyl)>-2-oxabicyclo<3.2.2>nonane-6,8-dione

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