(S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate

Base Information

• Chemical Name: (S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate
• CAS No.: 1430738-10-5
• Molecular Formula: C₂₉H₄₄N₂O₆Si
• Molecular Weight: 544.764
• Mol file: 1430738-10-5.mol

Synonyms:(S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate

Chemical Property of (S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate

There total 12 articles about (S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate 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: 79.0%

(S,E)-allyl 2-(2-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate (1430738-09-2) → (S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate (1430738-10-5)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; methanol; at 20 ℃;

Reference yield:

(S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-1-(5-methoxy-2-nitro-4-((triisopropyls11yl)oxy)benzoyl)pyrrolidin-3-one (1430738-05-8) → (S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate (1430738-10-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / -50 °C

2: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.5 h / Inert atmosphere

3: zinc; formic acid / ethanol / 0.33 h / 20 °C / Cooling with ice

4: pyridine / dichloromethane / -78 - 20 °C

5: acetic acid / tetrahydrofuran; methanol; water / 6 h / 20 °C

With pyridine; 2,6-dimethylpyridine; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; acetic acid; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; 2: |Suzuki Coupling;

Reference yield:

5-methoxy-2-nitro-4-((triisopropylsilyl)oxy)benzaldehyde (1430738-02-5) → (S,E)-allyl 2-(2-(hydroxymethyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-(triisopropylsilyloxy)phenylcarbamate (1430738-10-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dihydrogen peroxide; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate / tetrahydrofuran / 40 °C

2.1: benzotriazol-1-ol; dicyclohexyl-carbodiimide / dichloromethane / 0.5 h

2.2: 1 h / 0 °C / Inert atmosphere

3.1: trichloroisocyanuric acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 0.33 h / 0 - 20 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / -50 °C

5.1: potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 0.5 h / Inert atmosphere

6.1: zinc; formic acid / ethanol / 0.33 h / 20 °C / Cooling with ice

7.1: pyridine / dichloromethane / -78 - 20 °C

8.1: acetic acid / tetrahydrofuran; methanol; water / 6 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium chlorite; potassium phosphate; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; dihydrogen peroxide; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; 5.1: |Suzuki Coupling;

upstream raw materials:

((2S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxypyrrolidin-1-yl)( 5-methoxy-2-nitro-4-((triisopropylsilyl)oxy)phenyl)methanone

(S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-1-(5-methoxy-2-nitro-4-((triisopropyls11yl)oxy)benzoyl)pyrrolidin-3-one

(S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-1-(5-methoxy-2-nitro-4-((triisopropylsilyl)oxy)benzoyl)-4, 5-dihydro-1H-pyrrol-3-yl trifluoromethanesulfonate

(S,E)-(2-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-enyl)-2,3-dihydro-1H-pyrrol-1-yl)( 5-methoxy-2-nitro-4-( triisopropylsilyloxy)phenyl)methanone

Downstream raw materials:

allyl ((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1- oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate

allyl ((S)-1-(((S)-1-((4-((((2-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-((E)-prop-1-en-1-yl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-((triisopropylsilyl)oxy)phenyl)carbamoyl)oxy)methyl)phenyl)amino)-1-oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate

allyl ((S)-1-(((S)-1-((4-((((2-((S)-2-(hydroxymethyl)-4-((E)-prop-1-en-1-yl)-2,3-dihydro-1H-pyrrole-1-carbonyl)-4-methoxy-5-((triisopropylsilyl)oxy)phenyl)carbamoyl)oxy)methyl)phenyl)amino)-1-oxopropan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate

(11S,11aS)-4-((S)-2-((S)-2-(allyloxycarbonylamino)-3-methylbutanamido)propanamido)benzyl 11-hydroxy-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-8-(triisopropylsilyloxy)-11,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate