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

Base Information

• Chemical Name: (2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-4-methyl-5-oxopyrrolidine-2-carboxylic acid
• CAS No.: 1403577-26-3
• Molecular Formula: C₃₁H₄₃NO₈Si
• Molecular Weight: 585.77

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

Chemical Property of (2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-4-methyl-5-oxopyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-4-methyl-5-oxopyrrolidine-2-carboxylic acid

There total 21 articles about (2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-4-methyl-5-oxopyrrolidine-2-carboxylic acid 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: 63.0%

C31H43NO7Si (1403577-49-0) → (2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-4-methyl-5-oxopyrrolidine-2-carboxylic acid (1403577-26-3)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 20 ℃; for 13h; Inert atmosphere;

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,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-4-methyl-5-oxopyrrolidine-2-carboxylic acid (1403577-26-3)

Guidance literature:

Multi-step reaction with 17 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

14.1: ruthenium (IV) oxide monohydrate; sodium periodate / water; ethyl acetate / 20 °C

15.1: trimethylsilyl bromide / dichloromethane / 3 h / -30 - 20 °C / Inert atmosphere

16.1: Dess-Martin periodane / dichloromethane / 2 h / Inert atmosphere

17.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / tert-butyl alcohol / 13 h / 20 °C / 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; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; cerium(III) chloride; borane-THF; 2-methyl-but-2-ene; ruthenium (IV) oxide monohydrate; trimethylsilyl bromide; trimethylsiloxyethene; (±)-camphorsulfonic acid; tert.-butyl lithium; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; pentane;

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,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-4-methyl-5-oxopyrrolidine-2-carboxylic acid (1403577-26-3)

Guidance literature:

Multi-step reaction with 15 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

12.1: ruthenium (IV) oxide monohydrate; sodium periodate / water; ethyl acetate / 20 °C

13.1: trimethylsilyl bromide / dichloromethane / 3 h / -30 - 20 °C / Inert atmosphere

14.1: Dess-Martin periodane / dichloromethane / 2 h / Inert atmosphere

15.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / tert-butyl alcohol / 13 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; cerium(III) chloride; borane-THF; 2-methyl-but-2-ene; ruthenium (IV) oxide monohydrate; trimethylsilyl bromide; trimethylsiloxyethene; (±)-camphorsulfonic acid; tert.-butyl lithium; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 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

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