O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester

Base Information

• Chemical Name: O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester
• CAS No.: 263709-00-8
• Molecular Formula: C₁₈H₃₀N₂O₅Si
• Molecular Weight: 382.532

Synonyms:O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester

Chemical Property of O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester

There total 2 articles about O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl 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%

tert-butyldimethylsilyl chloride (18162-48-6) + L-threonine 2-(4-nitrophenyl)ethyl ester 4-methylbenzenesulfonate salt → O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester (263709-00-8)

Guidance literature:

With pyridine; 1H-imidazole; at 20 ℃; for 17h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<152::AID-HLCA152>3.0.CO;2-1

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester (263709-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / 17 h / 105 °C

2: 95 percent / pyridine; 1H-imidazole / 17 h / 20 °C

With pyridine; 1H-imidazole; 1: Esterification / 2: Etherification;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<152::AID-HLCA152>3.0.CO;2-1

Reference yield: 91.0%

1-N-methyl-3-phenoxycarbonylimidazolium chloride (64897-46-7) + O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester (263709-00-8) + 3’,5’-O-bis(t-butylsilyl)-2’-O-(t-butyldimethylsilyl)adenosine (212375-93-4) → C43H71N7O10Si3

Guidance literature:

1-N-methyl-3-phenoxycarbonylimidazolium chloride; 3’,5’-O-bis(t-butylsilyl)-2’-O-(t-butyldimethylsilyl)adenosine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester; With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.202002929

upstream raw materials:

tert-butyldimethylsilyl chloride

2-(4-nitrophenyl)ethanol

Downstream raw materials:

N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate

N-[[9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2-(methylthio)purin-6-yl]carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-(4-nitrophenyl)ethyl ester

N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine

N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine

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