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

Base Information

• Chemical Name: 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione
• CAS No.: 92098-16-3
• Molecular Formula: C₂₄H₂₆N₂O₆
• Molecular Weight: 438.48
• Mol file: 92098-16-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 45 articles about 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione 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:

1-acetyl-3-(3-benzyloxypropylidene)-2,5-piperazinedione (94807-44-0) → 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione (92098-16-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 4.32 g / 70percent hydrazine hydrate / dimethylformamide / 3 h / 0 °C

2: 1) NaH / 1) DMF, 0 deg C, 2 h, 2) DMF, 0 deg C, 2 h, then r.t., 12 h

3: 46 percent / OsO₄, NaClO₃ / dioxane; H₂O / 72 h / Ambient temperature

4: 94 percent / pyridinium p-toluenesulfonate / acetone / 24 h / Ambient temperature

5: 98 percent / H₂ / 10percent Pd/C / ethanol / 24 h / Ambient temperature

6: 12 percent / N-bromosuccinimide / CHCl₃ / 24 h / Ambient temperature

7: 83 percent / 2M HCl / tetrahydrofuran / 24 h / 50 °C

8: diethyl ether; tetrahydrofuran / 4 h / -30 °C

9: 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

10: tetrabutylammonium chloride, KF / CH₂Cl₂; acetonitrile / 12 h / 40 °C

11: methanol

With hydrogenchloride; methanol; dmap; sodium chlorate; potassium fluoride; N-Bromosuccinimide; osmium(VIII) oxide; tetrabutyl-ammonium chloride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; hydrazine hydrate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1246/bcsj.58.2812

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione (92098-16-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) NaH / 1) DMF, 0 deg C, 1 h, 2) DMF, 0 deg C, 2 h, then r.t., 12 h

2: 1) NaH / 1) DMF, 0 deg C, 1 h, 2) DMF, 0 deg C, 2 h, then r.t., 12 h

3: 92 percent / H₂ / 10percent Pd/C / ethanol / 24 h / Ambient temperature

4: 1) NaH / 1) DMF, 0 deg C, 1 h, 2) DMF, 0 deg C, 2 h, then r.t., 12 h

5: 99 percent / H₂ / 10percent Pd/C / ethanol / 24 h / Ambient temperature

6: 12 percent / N-bromosuccinimide / CHCl₃ / 24 h / Ambient temperature

7: 83 percent / 2M HCl / tetrahydrofuran / 24 h / 50 °C

8: diethyl ether; tetrahydrofuran / 4 h / -30 °C

9: 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

10: tetrabutylammonium chloride, KF / CH₂Cl₂; acetonitrile / 12 h / 40 °C

11: methanol

With hydrogenchloride; methanol; dmap; potassium fluoride; N-Bromosuccinimide; tetrabutyl-ammonium chloride; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1246/bcsj.58.2812

Reference yield:

3-(3-benzyloxy-1-hydroxypropyl)-3-hydroxy-3,1'-O-isopropylidene-2,5-piperazinedione → 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione (92098-16-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) NaH / 1) DMF, 0 deg C, 1 h, 2) DMF, 0 deg C, 2 h, then r.t., 12 h

2: 1) NaH / 1) DMF, 0 deg C, 1 h, 2) DMF, 0 deg C, 2 h, then r.t., 12 h

3: 92 percent / H₂ / 10percent Pd/C / ethanol / 24 h / Ambient temperature

4: 1) NaH / 1) DMF, 0 deg C, 1 h, 2) DMF, 0 deg C, 2 h, then r.t., 12 h

5: 99 percent / H₂ / 10percent Pd/C / ethanol / 24 h / Ambient temperature

6: 12 percent / N-bromosuccinimide / CHCl₃ / 24 h / Ambient temperature

7: 83 percent / 2M HCl / tetrahydrofuran / 24 h / 50 °C

8: diethyl ether; tetrahydrofuran / 4 h / -30 °C

9: 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

10: tetrabutylammonium chloride, KF / CH₂Cl₂; acetonitrile / 12 h / 40 °C

11: methanol

With hydrogenchloride; methanol; dmap; potassium fluoride; N-Bromosuccinimide; tetrabutyl-ammonium chloride; hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; acetonitrile;

DOI:10.1246/bcsj.58.2812

upstream raw materials:

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

(1S,6R)-5,6-Dihydroxy-7,9-bis-(4-methoxy-benzyl)-5-trimethylsilanylmethyl-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

5,6-dihydroxy-7,9-bis(p-methoxybenzyl)-5-trimethylsilylmethyl-2-oxa-7,9-diazabicyclo<4.2.2>decane-8.10-dione

p-Methoxybenzyl bromide

Downstream raw materials:

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

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

Aizumycin

(+/-)-bicyclomycin

Refernces

• 1、 Yamaura,Suzuki,Hashimoto,et al.. "A convenient synthesis of 6-hydroxy-7,9-bis(p-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo[4.2 .2]decane-8,10-dione". . p. 2812 - 2820. Retrieved 2007/10/02.
• 2、 Yamaura, Masanori,Suzuki, Tsuneji,Hashimoto, Hironobu,Yoshimura, Juji,Shin, Chung-gi. "A FACILE SYNTHESIS OF 7,9-DI-(p-METHOXYBENZYL)-7,9-DIAZA-5-METHYLENE-6-(t-BUTYLDIMETHYLSILYL)OXY-2-OXABICYCLODECANE-8,10-DIONE". . p. 1547 - 1548. Retrieved 2007/10/02.