5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane

Base Information

Chemical Name:5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane
CAS No.:861821-19-4
Molecular Formula:C₃₃H₄₃N₂O₈P
Molecular Weight:626.687
Hs Code.:

Synonyms:5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane

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Chemical Property of 5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane

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Technology Process of 5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane

There total 5 articles about 5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane 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:

: 861821-16-1
3(R),5(S),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-3-hydroxy-2,5-dimethyl-2-nitroheptane

: 2161-16-2
phosphorous acid ethyl ester-diphenyl ester

: 861821-19-4
5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane

Guidance literature:: phosphorous acid ethyl ester-diphenyl ester; With iodine; In dichloromethane; at -15 ℃; for 0.5h;

3(R),5(S),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-3-hydroxy-2,5-dimethyl-2-nitroheptane; With pyridine; In dichloromethane; at -15 - 20 ℃; for 18h;
DOI:10.1021/ja051657t

Reference yield:

: 861821-14-9
3(S),4(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-3-methyl-pentanal

: 861821-19-4
5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium tert-butoxide / acetonitrile; 2-methyl-propan-2-ol / 24 h / 0 - 20 °C

2.1: I₂ / CH₂Cl₂ / 0.5 h / -15 °C

2.2: pyridine / CH₂Cl₂ / 18 h / -15 - 20 °C

With potassium tert-butylate; iodine; In dichloromethane; acetonitrile; tert-butyl alcohol; 1.1: Henry reaction;
DOI:10.1021/ja051657t

Reference yield:

: (5S),(6S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-3-hydroxy-2,5-dimethyl-2-nitroheptane

: 861821-19-4
5(S),3(R),6(S)-[N-benzyl-N-(tert-butyloxycarbonyl)]amino-2,5-dimethyl-2-nitro-3-(diphenylphosphatoxy)heptane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 91 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / 1.83 h / -78 - 20 °C

2.1: BH3*Me2S; (R)-(-)-α,α-diphenyl-2-pyrrolidinemethanol / tetrahydrofuran; toluene / 45 °C

3.1: I₂ / CH₂Cl₂ / 0.5 h / -15 °C

3.2: pyridine / CH₂Cl₂ / 18 h / -15 - 20 °C

With oxalyl dichloride; dimethylsulfide borane complex; iodine; (R)-α,α-diphenylprolinol; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Swern oxidation;
DOI:10.1021/ja051657t