N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin

Base Information

• Chemical Name: N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin
• CAS No.: 92098-17-4
• Molecular Formula: C₃₁H₃₈N₂O₉
• Molecular Weight: 582.651
• Mol file: 92098-17-4.mol

Synonyms:N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin

Chemical Property of N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin

There total 17 articles about N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin 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:

8,10-bis(p-methoxybenzyl)-8,10-diaza-5-<(methylsulfonyl)methyl>-2-oxabicyclo<4.2.2>decane-7,9-dione (95782-41-5) → N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin (92098-17-4)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / ethanol / 0.33 h / 45 °C

2: 95.5 percent / 30percent H₂O₂ / tetrahydrofuran / 0.33 h / Heating

3: 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

4: 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; In tetrahydrofuran; ethanol;

DOI:10.1021/ja00297a035

Reference yield:

8,10-bis(p-methoxybenzyl)-8,10-diaza-5-(hydroxymethyl)-2-oxabicyclo<4.2.2>decane-7,9-dione (92098-12-9) → N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin (92098-17-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 12 h / Ambient temperature

2: NaBH₄ / ethanol / 0.33 h / 45 °C

3: 95.5 percent / 30percent H₂O₂ / tetrahydrofuran / 0.33 h / Heating

4: 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

5: 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; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1021/ja00297a035

Reference yield:

1,4-bis(p-methoxybenzyl)-3-(2'-thiopyridyl)-6-<1''-(hydroxymethyl)-3''-<((tert-butyldimethylsilyl)oxy)propyl>>-2,5-piperazinedione (95694-62-5) → N,N'-bis(p-methoxybenzyl)-2',3'-O-isopropylidene-bicyclomycin (92098-17-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / Et₃N / tetrahydrofuran / 0.58 h / Ambient temperature

2: 83 percent / Cu(ClO₄)2 / tetrahydrofuran / 16 h / Ambient temperature

3: 99 percent / NaBH₄ / ethanol / 0.33 h / Heating

4: 83 percent / 30percent H₂O₂ / tetrahydrofuran / 0.25 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; copper(II) perchlorate; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1021/ja00297a035

upstream raw materials:

(+/-)-2,2,4-trimethyl-1,3-dioxolane-4-carboxaldehyde

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

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

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

Downstream raw materials:

(+/-)-bicyclomycin

N,N'-bis(p-methoxybenzyl)-1'-O-(trifluoroacetyl)-2',3'-O-isopropylidene-bicyclomycin