(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
CAS No.:212772-63-9
Molecular Formula:C₂₅H₃₉NO₆Si
Molecular Weight:477.673
Hs Code.:

(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Synonyms:(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

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Chemical Property of (2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

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Technology Process of (2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

There total 11 articles about (2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl 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:

: (2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-4-methyl-2-((S)-2-methyl-1-trimethylsilanyloxy-allyl)-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

: 212772-63-9
(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: With water; ammonium chloride; In tetrahydrofuran; for 0.5h; Yield given;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

Reference yield:

: 20839-80-9
(4-methoxybenzylamino)acetic acid methyl ester

: 212772-63-9
(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: Et₃N / CH₂Cl₂ / 1 h / 23 °C

2: 93 percent / LDA / tetrahydrofuran / 2 h / -78 °C

3: 90 percent / DBU / 1.) THF, -0 deg C, 15 min, 2.) THF, H₂O, -78 deg C, 0.5 h

4: 95 percent / NaBH(OAc)3 / acetic acid / 1 h / 23 °C

5: 85 percent / pyridine / 10 h / 23 °C

6: 98 percent / 2,6-lutidine / 12 h / 23 °C

7: 92 percent / NaOMe, MeOH / 5 h / 23 °C

8: 82 percent / Raney Ni / ethanol / 1 h / 0 °C

9: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / 23 °C

10: tetrahydrofuran / 0.5 h / -40 °C

11: NH₄Cl, H₂O / tetrahydrofuran / 0.5 h

With pyridine; 2,6-dimethylpyridine; methanol; water; sodium methylate; sodium tris(acetoxy)borohydride; nickel; ammonium chloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

Reference yield:

: 212772-59-3
(R)-1-(4-Methoxy-benzyl)-4-methyl-4-methylsulfanyl-3,5-dioxo-pyrrolidine-2-carboxylic acid methyl ester

: 212772-63-9
(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-2-methyl-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / DBU / 1.) THF, -0 deg C, 15 min, 2.) THF, H₂O, -78 deg C, 0.5 h

2: 95 percent / NaBH(OAc)3 / acetic acid / 1 h / 23 °C

3: 85 percent / pyridine / 10 h / 23 °C

4: 98 percent / 2,6-lutidine / 12 h / 23 °C

5: 92 percent / NaOMe, MeOH / 5 h / 23 °C

6: 82 percent / Raney Ni / ethanol / 1 h / 0 °C

7: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / 23 °C

8: tetrahydrofuran / 0.5 h / -40 °C

9: NH₄Cl, H₂O / tetrahydrofuran / 0.5 h

With pyridine; 2,6-dimethylpyridine; methanol; water; sodium methylate; sodium tris(acetoxy)borohydride; nickel; ammonium chloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T