(5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal

Base Information

Chemical Name:(5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal
CAS No.:919521-68-9
Molecular Formula:C₃₅H₄₈N₄O₉
Molecular Weight:668.788
Hs Code.:

Synonyms:(5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal

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Chemical Property of (5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal

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Technology Process of (5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal

There total 14 articles about (5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal 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: 78.0%

: 919521-48-5
(5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal

: 5416-93-3
4-Methoxyphenyl isocyanate

: 919521-68-9
(5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal

Guidance literature:: In benzene; at 20 ℃; for 0.5h;
DOI:10.1021/ol062282z

Reference yield:

: 121352-65-6
(2R,3R)-3-(4-[(1,1-dimethylethyl)dimethylsilyloxy]butyl)oxirane-2-methanol

: 919521-68-9
(5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal

Guidance literature:: Multi-step reaction with 12 steps

1: 94 percent / Red-Al(R) / CH₂Cl₂; toluene / 5 h / -20 - 0 °C

2: 95 percent / PPTS / CH₂Cl₂ / 0.42 h / 0 °C

3: 87 percent / DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -5 °C

4: 97 percent / DMSO; oxalyl chloride; DIPEA / CH₂Cl₂ / -78 - 0 °C

5: 89 percent / DIPEA / (R,R)-cyclohexane-1,2-(N=CH-3,5-tBu₂-C₆H₂-2-O-)2Co / CH₂Cl₂ / 60 h / -40 °C

6: HCO₂NH₄ / Pd/C / methanol / 3 h / 20 °C

7: 1.40 g / acetonitrile / 0.5 h / 20 °C

8: pyridine; DMAP / CH₂Cl₂ / 0.25 h / 20 °C

9: 81 mg / DIPEA / acetonitrile / 80 °C

10: 100 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

11: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

12: 78 percent / benzene / 0.5 h / 20 °C

With pyridine; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; ammonium formate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; acetonitrile; benzene; 4: Swern oxidation / 11: Dess-Martin oxidation;
DOI:10.1021/ol062282z

Reference yield:

: 919521-43-0
(R)-7-(tert-butyldimethylsiloxy)heptane-1,3-diol

: 919521-68-9
(5R,4'R)-6-[N,3'-bis(tert-butoxycarbonyl)-1'-(p-methoxyphenylcarbamoyl)-2'-iminoimidazolidin-4'-yl]-5-(p-methoxybenzyloxy)hexanal

Guidance literature:: Multi-step reaction with 11 steps

1: 95 percent / PPTS / CH₂Cl₂ / 0.42 h / 0 °C

2: 87 percent / DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -5 °C

3: 97 percent / DMSO; oxalyl chloride; DIPEA / CH₂Cl₂ / -78 - 0 °C

4: 89 percent / DIPEA / (R,R)-cyclohexane-1,2-(N=CH-3,5-tBu₂-C₆H₂-2-O-)2Co / CH₂Cl₂ / 60 h / -40 °C

5: HCO₂NH₄ / Pd/C / methanol / 3 h / 20 °C

6: 1.40 g / acetonitrile / 0.5 h / 20 °C

7: pyridine; DMAP / CH₂Cl₂ / 0.25 h / 20 °C

8: 81 mg / DIPEA / acetonitrile / 80 °C

9: 100 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

10: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

11: 78 percent / benzene / 0.5 h / 20 °C

With pyridine; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; ammonium formate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; benzene; 3: Swern oxidation / 10: Dess-Martin oxidation;
DOI:10.1021/ol062282z