(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:1403577-21-8
Molecular Formula:C₄₀H₆₃NO₇Si
Molecular Weight:698.028
Hs Code.:

(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 16 articles about (2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-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: 76.0%

: 1403577-18-3
(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-3-[(E)-propenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1403577-19-4
(E)-(S)-1-bromo-2,5,5-trimethylhex-3-ene

: 1403577-21-8
(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: (E)-(S)-1-bromo-2,5,5-trimethylhex-3-ene; With cerium(III) chloride; tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - -40 ℃; for 13h; Inert atmosphere;

(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-2-methoxymethoxymethyl-4-methyl-3-[(E)-propenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester; In tetrahydrofuran; pentane; at -78 ℃; for 2h; 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

: 1403577-21-8
(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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

With 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; tert.-butyl lithium; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane;
DOI:10.1021/ol302541j DOI:10.1021/ol302541j

Reference yield:

: C₃₀H₄₁NO₅Si

: 1403577-21-8
(2S,3S,4S)-2-(tert-butyldiphenylsilanyloxymethyl)-3-hydroxy-3-[(E)-(1S,3R)-1-hydroxy-3,6,6-trimethylhept-4-enyl]-2-methoxymethoxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium carbonate; methanol

2.1: lithium bromide; toluene-4-sulfonic acid

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

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

5.1: diethyl ether / 2 h / -78 °C

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

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

7.2: Inert atmosphere

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

8.2: 2 h / -78 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; methanol; cerium(III) chloride; borane-THF; trimethylsiloxyethene; tert.-butyl lithium; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; lithium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane;
DOI:10.1021/ol302541j DOI:10.1021/ol302541j