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

Base Information

Chemical Name:(2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-hydroxycarbonyl-1-methyl-4-methyl-5-oxopyrrolidine
CAS No.:1403577-25-2
Molecular Formula:C₃₂H₄₅NO₈Si
Molecular Weight:599.797
Hs Code.:

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

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

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

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

There total 23 articles about (2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-hydroxycarbonyl-1-methyl-4-methyl-5-oxopyrrolidine 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:

: C₃₂H₄₅NO₇Si

: 1403577-25-2
(2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-hydroxycarbonyl-1-methyl-4-methyl-5-oxopyrrolidine

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:

: 1403577-31-0
(R)-2-acetoxymethyl-2-hydroxymethyl-4-methyl-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

: 1403577-25-2
(2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-hydroxycarbonyl-1-methyl-4-methyl-5-oxopyrrolidine

Guidance literature:: Multi-step reaction with 19 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: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h / 20 °C / Inert atmosphere

16.1: caesium carbonate / 36 h / 50 °C / Inert atmosphere

17.1: trifluoroacetic acid / dichloromethane; methanol / 5 h / 20 °C / Inert atmosphere

18.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

19.1: 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; triethylsilane; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; cerium(III) chloride; borane-THF; 2-methyl-but-2-ene; ruthenium (IV) oxide monohydrate; trimethylsiloxyethene; (±)-camphorsulfonic acid; tert.-butyl lithium; potassium carbonate; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; trifluoroacetic acid; 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

: 1403577-25-2
(2S,3S,4R)-3-[(1S,3R)-4-acetoxy-1-methoxy-3-methylbutyl]-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-hydroxycarbonyl-1-methyl-4-methyl-5-oxopyrrolidine

Guidance literature:: Multi-step reaction with 17 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: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h / 20 °C / Inert atmosphere

14.1: caesium carbonate / 36 h / 50 °C / Inert atmosphere

15.1: trifluoroacetic acid / dichloromethane; methanol / 5 h / 20 °C / Inert atmosphere

16.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

17.1: 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; triethylsilane; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; cerium(III) chloride; borane-THF; 2-methyl-but-2-ene; ruthenium (IV) oxide monohydrate; trimethylsiloxyethene; (±)-camphorsulfonic acid; tert.-butyl lithium; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; trifluoroacetic acid; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; pentane;
DOI:10.1021/ol302541j DOI:10.1021/ol302541j