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

Base Information

Chemical Name:(2S,3S,4S)-3-buten-1-yl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate
CAS No.:127084-38-2
Molecular Formula:C₃₇H₅₁N₃O₄Si₂
Molecular Weight:658.001
Hs Code.:

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

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

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

There total 30 articles about (2S,3S,4S)-3-buten-1-yl 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: 95.0%

: 69739-34-0
t-butyldimethylsiyl triflate

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

: 127084-38-2
(2S,3S,4S)-3-buten-1-yl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

Guidance literature:: With 2,6-dimethylpyridine; In tetrahydrofuran; -78 to 25 deg C;
DOI:10.1021/jo00016a014

Reference yield: 90.0%

: 627-27-0
homoalylic alcohol

: 172170-21-7
ethyl (2S,3S,4S)-2-azido-4-(4-tert-butyldimethylsilyloxyphenyl)-4-tert-butyldiphenylsilyloxy-3-methylbutanoate

: 127084-38-2
(2S,3S,4S)-3-buten-1-yl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

Guidance literature:: With titanium(IV) isopropylate; In benzene;
DOI:10.1016/0957-4166(95)00282-T

Reference yield:

: 95592-67-9
4-pivaloyloxybenzaldehyde

: 127084-38-2
(2S,3S,4S)-3-buten-1-yl 2-azido-4-<4-<(tert-butyldimethylsilyl)oxy>phenyl>-4-<(tert-butyldiphenylsilyl)oxy>-3-methylbutanoate

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; sodium azide; dimethylsulfide; methyltriphenoxyphosphonium iodide; ozone; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00016a014