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

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Chemical Name:4-benzyloxy-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)-2-hydroxyethyl]-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:792922-86-2
Molecular Formula:C₂₉H₄₁NO₉
Molecular Weight:547.646
Hs Code.:

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

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

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

There total 13 articles about 4-benzyloxy-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)-2-hydroxyethyl]-3-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: 62.0%

: 792922-83-9
4-benzyloxy-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

: 792922-86-2
4-benzyloxy-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)-2-hydroxyethyl]-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: 4-benzyloxy-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)allyl]-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester; With ozone; In methanol; at -78 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;
DOI:10.1021/jo048924i

Reference yield:

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

: 792922-86-2
4-benzyloxy-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)-2-hydroxyethyl]-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 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: 1.22 g / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

5.1: O₃ / methanol / 0.5 h / -78 °C

5.2: 62 percent / NaBH₄ / methanol / 1 h / 0 °C

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

Reference yield:

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

: 792922-86-2
4-benzyloxy-2-[1-(3,5-dimethoxy-2-methoxymethoxy-4-methylphenyl)-2-hydroxyethyl]-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 30.4 g / Et₃N / CH₂Cl₂ / 4 h / 25 °C

2.1: 86 percent / Et₃Al / NiCl₂(dppp) / toluene / 0 - 25 °C

3.1: 72 percent / PhIO; I₂ / CH₂Cl₂ / 24 h / 25 °C

4.1: 97 percent / K₂CO₃ / methanol; H₂O / 4 h / 20 °C

5.1: NaH; n-Bu₄NI / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C

5.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

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

6.2: 1.22 g / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

7.1: O₃ / methanol / 0.5 h / -78 °C

7.2: 62 percent / NaBH₄ / methanol / 1 h / 0 °C

With samarium diiodide; iodosylbenzene; tributyltin chloride; iodine; triethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo048924i