3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:792922-94-2
Molecular Formula:C₃₁H₄₂N₂O₉
Molecular Weight:586.682
Hs Code.:

3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of 3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of 3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

There total 10 articles about 3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester 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:

: 792922-81-7
acetic acid 1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl ester

: 3-benzyloxycarbonylamino-2,4-dihydroxypyrrolidine-1-carboxylic acid tert-butyl ester

: 792922-94-2
3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: acetic acid 1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl ester; With samarium diiodide; tributyltin chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 12h;

3-benzyloxycarbonylamino-2,4-dihydroxypyrrolidine-1-carboxylic acid tert-butyl ester; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo048924i

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 792922-94-2
3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2.35 g / Et₃N / CH₂Cl₂ / 3 h / 25 °C

2.1: aq. NaOH; t-BuOCl; (DHQD)2AQN / K₂OsO₄*2H₂O / propan-1-ol / 6 h / 0 °C

3.1: 112.0 g / (NH₄)3Ce(NO₃)6 / acetonitrile; H₂O / 0.08 h / 25 °C

4.1: 67 percent / i-Bu₂AlH / tetrahydrofuran / 14 h / -78 °C

5.1: SmI₂; n-Bu₃SnCl / Pd(PPh₃)4 / tetrahydrofuran / 12 h / 25 °C

5.2: 838.0 mg / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

With sodium hydroxide; samarium diiodide; hydroquinidine anthraquinone-1,4-diyl diether; tert-butylhypochlorite; (NH₄)3Ce(NO₃)6; tributyltin chloride; diisobutylaluminium hydride; triethylamine; potassium osmate(VI); tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; propan-1-ol; dichloromethane; water; acetonitrile; 2.1: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/jo048924i

Reference yield:

: 19676-67-6
2,4-dimethoxy-3-methylphenol

: 792922-94-2
3-benzyloxycarbonylamino-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

1.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

2.2: 86 percent / tetrahydrofuran; hexane / 0 - 25 °C

3.1: 89 percent / Et₃N; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

4.1: SmI₂; n-Bu₃SnCl / Pd(PPh₃)4 / tetrahydrofuran / 12 h / 25 °C

4.2: 838.0 mg / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

With dmap; n-butyllithium; samarium diiodide; tributyltin chloride; sodium hydride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo048924i