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

Base Information

• Chemical Name: (2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 212772-62-8
• Molecular Formula: C₂₂H₃₃NO₆Si
• Molecular Weight: 435.593

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

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

Chemical Property:

Purity/Quality:

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

There total 9 articles about (2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-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: 95.0%

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester → (2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (212772-62-8)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 23 ℃; for 1h;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

Reference yield:

(4-methoxybenzylamino)acetic acid methyl ester (20839-80-9) → (2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (212772-62-8)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 2,6-dimethylpyridine; methanol; sodium methylate; sodium tris(acetoxy)borohydride; nickel; 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:

(R)-1-(4-Methoxy-benzyl)-4-methyl-4-methylsulfanyl-3,5-dioxo-pyrrolidine-2-carboxylic acid methyl ester (212772-59-3) → (2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester (212772-62-8)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 2,6-dimethylpyridine; methanol; sodium methylate; sodium tris(acetoxy)borohydride; nickel; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; dichloromethane; acetic acid;

DOI:10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO;2-T

upstream raw materials:

(4-methoxybenzylamino)acetic acid methyl ester

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

(5R,4S,3R)-4-hydroxy-5-hydroxymethyl-1-(4-methoxybenzyl)-3-methyl-3-methylsulfanyl-2-oxo-pyrrolidine-5-carboxylic acid methyl ester

(5R,4R,3R)-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-1-(4-methoxybenzyl)-3-methyl-3-methylsulfanyl-2-oxo-pyrrolidine-5-carboxylic acid methyl ester

Downstream raw materials:

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

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

(1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione

(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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