(2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1403577-23-0
• Molecular Formula: C₃₈H₅₉NO₉Si
• Molecular Weight: 701.973

Synonyms:(2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester

There total 18 articles about (2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-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: 98.0%

(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(1S,3R)-4-hydroxy-1-methoxy-3-methyl-butyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1403577-36-5) + acetic anhydride (108-24-7) → (2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester (1403577-23-0)

Guidance literature:

With pyridine; for 16h; Inert atmosphere;

DOI:10.1021/ol302541j DOI:10.1021/ol302541j

Reference yield:

(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester → (2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester (1403577-23-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium bromide; toluene-4-sulfonic acid

2.1: borane-THF / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

4.1: diethyl ether / 2 h / -78 °C

5.1: trimethylsiloxyethene; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 7 h / Reflux; Inert atmosphere

6.1: ozone / dichloromethane / -78 - 20 °C / Inert atmosphere

6.2: Inert atmosphere

7.1: tert.-butyl lithium; cerium(III) chloride / tetrahydrofuran; pentane / 13 h / -78 - -40 °C / Inert atmosphere

7.2: 2 h / -78 °C / Inert atmosphere

8.1: (±)-camphorsulfonic acid / 12 h / Inert atmosphere

9.1: dichloromethane / 20 °C / Inert atmosphere

10.1: ozone / dichloromethane; methanol / 0.33 h / -78 °C / Inert atmosphere

10.2: 5 h / -78 - 0 °C / Inert atmosphere

11.1: pyridine / 16 h / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; cerium(III) chloride; borane-THF; trimethylsiloxyethene; (±)-camphorsulfonic acid; tert.-butyl lithium; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; pentane;

DOI:10.1021/ol302541j DOI:10.1021/ol302541j

Reference yield:

(R)-2-acetoxymethyl-2-hydroxymethyl-4-methyl-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (1403577-31-0) → (2S,3S,4S)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyl-diphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methylpyrrolidine-1-carboxylic acid tert-butyl ester (1403577-23-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 1H-imidazole; dmap / dichloromethane / 2 h / Inert atmosphere

2.1: potassium carbonate; methanol

3.1: lithium bromide; toluene-4-sulfonic acid

4.1: borane-THF / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

6.1: diethyl ether / 2 h / -78 °C

7.1: trimethylsiloxyethene; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 7 h / Reflux; Inert atmosphere

8.1: ozone / dichloromethane / -78 - 20 °C / Inert atmosphere

8.2: Inert atmosphere

9.1: tert.-butyl lithium; cerium(III) chloride / tetrahydrofuran; pentane / 13 h / -78 - -40 °C / Inert atmosphere

9.2: 2 h / -78 °C / Inert atmosphere

10.1: (±)-camphorsulfonic acid / 12 h / Inert atmosphere

11.1: dichloromethane / 20 °C / Inert atmosphere

12.1: ozone / dichloromethane; methanol / 0.33 h / -78 °C / Inert atmosphere

12.2: 5 h / -78 - 0 °C / Inert atmosphere

13.1: pyridine / 16 h / Inert atmosphere

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; dmap; cerium(III) chloride; borane-THF; trimethylsiloxyethene; (±)-camphorsulfonic acid; tert.-butyl lithium; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; pentane;

DOI:10.1021/ol302541j DOI:10.1021/ol302541j

upstream raw materials:

(R)-2-acetoxymethyl-2-hydroxymethyl-4-methyl-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

4-Methyl-1H-pyrrole-2-carboxylic acid ethyl ester

(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-4-methyl-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

(2S,3R,4S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester

(2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-5-oxo-pyrrolidine

(2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-1-methyl-4-methyl-5-oxopyrrolidine

(2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-hydroxymethyl-1-methyl-4-methyl-5-oxopyrrolidine

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