2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate

Base Information

• Chemical Name: 2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate
• CAS No.: 213976-31-9
• Molecular Formula: C₃₉H₄₈N₄O₆Si₂
• Molecular Weight: 725.004

Synonyms:2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate

Chemical Property of 2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate

There total 21 articles about 2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate 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: 44.0%

(2S,3S,4S)-2-Azido-4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butyric acid + 2-hydroxynitrobenzene (88-75-5,78813-12-4) → 2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate (213976-31-9)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 25 ℃; for 12h;

DOI:10.1016/S0040-4020(98)00647-4

Reference yield:

p-[(tert-butyldimethylsilyl)oxy]benzaldehyde (120743-99-9) → 2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate (213976-31-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 36 percent / Zn dust / benzene / 1.5 h / Heating

2.1: 76 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

3.1: Amano P lipase / various solvent(s) / 7 h / 33 °C / Enzymatic reaction

4.1: 97 percent / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 44 h / 20 °C

5.1: 99 percent / HAl(i-Bu)2 / toluene / 1 h / -78 °C

6.1: oxalyl chloride; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1.67 h / -78 °C

7.1: tert-BuLi / tetrahydrofuran; pentane / 2 h / -78 °C

8.1: 47 percent / O₃; dimethylsulfide / CH₂Cl₂ / 1.5 h / -78 °C

9.1: 77 percent / I₂; triphenylphosphine; imidazole / diethyl ether; acetonitrile / 12 h / 20 °C

10.1: 88 percent / NaN₃ / dimethylformamide / 1 h / 60 °C

11.1: 90 percent / Ti(O-i-Pr)4 / 2 h / Heating

12.1: ozone / CH₂Cl₂; methanol / 30 h / -78 °C

12.2: Me₂S; DBU; 0.1 M aq. citric acid / CH₂Cl₂; methanol / 4 h / 20 °C

13.1: 44 percent / DCC / tetrahydrofuran / 12 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; dimethylsulfide; Amano P lipase; iodine; tert.-butyl lithium; diisobutylaluminium hydride; ozone; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; benzene; 1.1: Addition / 2.1: Reduction / 3.1: Acetylation / 4.1: Substitution / 5.1: reductive deacetylation / 6.1: Oxidation / 7.1: Addition / 8.1: ozonolysis / 9.1: Iodination / 10.1: Substitution / 11.1: transesterification / 12.1: ozonolysis / 12.2: Hydrolysis / 13.1: Esterification;

DOI:10.1016/S0040-4020(98)00647-4

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 2-nitrophenyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate (213976-31-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 85 percent / imidazole / CH₂Cl₂ / 0.67 h / 0 °C

2.1: 36 percent / Zn dust / benzene / 1.5 h / Heating

3.1: 76 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

4.1: Amano P lipase / various solvent(s) / 7 h / 33 °C / Enzymatic reaction

5.1: 97 percent / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 44 h / 20 °C

6.1: 99 percent / HAl(i-Bu)2 / toluene / 1 h / -78 °C

7.1: oxalyl chloride; Et₃N / CH₂Cl₂; dimethylsulfoxide / 1.67 h / -78 °C

8.1: tert-BuLi / tetrahydrofuran; pentane / 2 h / -78 °C

9.1: 47 percent / O₃; dimethylsulfide / CH₂Cl₂ / 1.5 h / -78 °C

10.1: 77 percent / I₂; triphenylphosphine; imidazole / diethyl ether; acetonitrile / 12 h / 20 °C

11.1: 88 percent / NaN₃ / dimethylformamide / 1 h / 60 °C

12.1: 90 percent / Ti(O-i-Pr)4 / 2 h / Heating

13.1: ozone / CH₂Cl₂; methanol / 30 h / -78 °C

13.2: Me₂S; DBU; 0.1 M aq. citric acid / CH₂Cl₂; methanol / 4 h / 20 °C

14.1: 44 percent / DCC / tetrahydrofuran / 12 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; lithium aluminium tetrahydride; sodium azide; oxalyl dichloride; dimethylsulfide; Amano P lipase; iodine; tert.-butyl lithium; diisobutylaluminium hydride; ozone; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; benzene; 1.1: Substitution / 2.1: Addition / 3.1: Reduction / 4.1: Acetylation / 5.1: Substitution / 6.1: reductive deacetylation / 7.1: Oxidation / 8.1: Addition / 9.1: ozonolysis / 10.1: Iodination / 11.1: Substitution / 12.1: transesterification / 13.1: ozonolysis / 13.2: Hydrolysis / 14.1: Esterification;

DOI:10.1016/S0040-4020(98)00647-4

upstream raw materials:

2-hydroxynitrobenzene

(2S,3S,4S)-3-buten-1-yl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

p-[(tert-butyldimethylsilyl)oxy]benzaldehyde

4-hydroxy-benzaldehyde

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