2-Oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,9-bis[(4-methoxyphenyl)methyl] -5-methylene-, (1R)-

Base Information

• Chemical Name: 2-Oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,9-bis[(4-methoxyphenyl)methyl] -5-methylene-, (1R)-
• CAS No.: 95341-59-6
• Molecular Formula: C30H40N2O6Si
• Molecular Weight: 552.743
• Mol file: 95341-59-6.mol

Synonyms:

Chemical Property of 2-Oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,9-bis[(4-methoxyphenyl)methyl] -5-methylene-, (1R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,9-bis[(4-methoxyphenyl)methyl] -5-methylene-, (1R)-

There total 28 articles about 2-Oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,9-bis[(4-methoxyphenyl)methyl] -5-methylene-, (1R)- 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: 80.2%

t-butyldimethylsiyl triflate (69739-34-0) + 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione (92098-16-3) → 6-(t-butyldimethylsilyloxy)-1,9-bis(p-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo<4.2.2>decane-8,10-dione (94807-54-2,95341-59-6,117249-39-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1246/bcsj.58.2812

Reference yield: 80.0%

tert-butyldimethylsilyl triflate (133732-91-9) + 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione (92098-16-3) → 6-(t-butyldimethylsilyloxy)-1,9-bis(p-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo<4.2.2>decane-8,10-dione (94807-54-2,95341-59-6,117249-39-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1246/cl.1984.1547

Reference yield:

1-acetyl-3-(3-benzyloxypropylidene)-2,5-piperazinedione (94807-44-0) → 6-(t-butyldimethylsilyloxy)-1,9-bis(p-methoxybenzyl)-5-methylene-2-oxa-7,9-diazabicyclo<4.2.2>decane-8,10-dione (94807-54-2,95341-59-6,117249-39-5)

Guidance literature:

Multi-step reaction with 12 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

12: 80.2 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / Ambient temperature

With 2,6-dimethylpyridine; 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

upstream raw materials:

t-butyldimethylsiyl triflate

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

tert-butyldimethylsilyl triflate

p-Methoxybenzyl bromide

Downstream raw materials:

(1R,6S)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1R,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

(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-1-[(S)-hydroxy-((S)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-methyl]-7,9-bis-(4-methoxy-benzyl)-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione

(1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-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

Aizumycin

Refernces

• 1、 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.