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

Base Information

Chemical Name:(2S,3S,4S)-4-nitrophenyl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate
CAS No.:131068-86-5
Molecular Formula:C₃₉H₄₈N₄O₆Si₂
Molecular Weight:725.004
Hs Code.:

Synonyms:(2S,3S,4S)-4-nitrophenyl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

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Chemical Property of (2S,3S,4S)-4-nitrophenyl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

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Technology Process of (2S,3S,4S)-4-nitrophenyl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

There total 31 articles about (2S,3S,4S)-4-nitrophenyl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-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: 43.0%

: 100-02-7,78813-13-5,89830-32-0
4-nitro-phenol

: (2S,3S,4S)-2-Azido-4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butyric acid

: 131068-86-5
(2S,3S,4S)-4-nitrophenyl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

Guidance literature:: With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 25 ℃; for 12h;
DOI:10.1016/S0040-4020(98)00647-4

Reference yield:

: 95592-67-9
4-pivaloyloxybenzaldehyde

: 131068-86-5
(2S,3S,4S)-4-nitrophenyl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

Guidance literature:: Multi-step reaction with 11 steps

2: 97 percent / imidazole, DMAP / dimethylformamide / 12 h / 60 °C

3: 1.) ozone 2.) Me₂S / CH₂Cl₂/MeOH 1:1, 1.) -78 2.) 12 h r.t.

5: 85 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 18 h

6: 91 percent / NaN₃ / dimethylformamide / 1 h / 60 °C

7: 91 percent / Ti(Oi-Pr)4 / benzene / 6 h / Heating

8: 95 percent / 2,6-lutidine / tetrahydrofuran / -78 to 25 deg C

9: 1.) ozone 2.) Me₂S / CH₂Cl₂/MeOH 1:1, 1.) -78 deg C 2.) 4 h, 25 deg C

10: DBU / 2 h

11: DCC / tetrahydrofuran / 12 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; sodium azide; dimethylsulfide; methyltriphenoxyphosphonium iodide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00016a014

Reference yield:

: 131068-80-9
(3S,4S)-4-hydroxy-3-methyl-4-<4-<(2,2-dimethylpropanoyl)oxy>phenyl>butene

: 131068-86-5
(2S,3S,4S)-4-nitrophenyl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / imidazole, DMAP / dimethylformamide / 12 h / 60 °C

2: 1.) ozone 2.) Me₂S / CH₂Cl₂/MeOH 1:1, 1.) -78 2.) 12 h r.t.

4: 85 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 18 h

5: 91 percent / NaN₃ / dimethylformamide / 1 h / 60 °C

6: 91 percent / Ti(Oi-Pr)4 / benzene / 6 h / Heating

7: 95 percent / 2,6-lutidine / tetrahydrofuran / -78 to 25 deg C

8: 1.) ozone 2.) Me₂S / CH₂Cl₂/MeOH 1:1, 1.) -78 deg C 2.) 4 h, 25 deg C

9: DBU / 2 h

10: DCC / tetrahydrofuran / 12 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; sodium azide; dimethylsulfide; methyltriphenoxyphosphonium iodide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00016a014