(4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal

Base Information

Chemical Name:(4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal
CAS No.:512171-77-6
Molecular Formula:C₃₄H₄₃NO₅Si
Molecular Weight:573.805
Hs Code.:

Synonyms:(4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal

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Chemical Property of (4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal

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Technology Process of (4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal

There total 8 articles about (4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal 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:

: 512171-76-5
(+)-(4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexen-1-ol

: 512171-77-6
(4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 5h;
DOI:10.1021/jo026817n

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 512171-77-6
(4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / DMAP / acetonitrile / 0.17 h

2: 95 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / 0 °C

3: 2-iodoxybenzoic acid / dimethylsulfoxide / 5 h / 20 °C

With dmap; lithium aluminium tetrahydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/jo026817n

Reference yield:

: 148968-08-5
(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone

: 512171-77-6
(4Z)-(2R,3S)-3-(t-butyloxycarbonyl)amino-2-benzyloxy-6-(t-butyldiphenylsilyloxy)-4-hexenal

Guidance literature:: Multi-step reaction with 7 steps

1: benzene / 24 h / Heating

2: 7.39 g / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

3: DMAP; imidazole / dimethylformamide / 24 h / 20 °C

4: 47 percent / (NH₄)2Ce(NO₃)6 / H₂O; acetonitrile / 0.5 h / 0 °C

5: 84 percent / DMAP / acetonitrile / 0.17 h

6: 95 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / 0 °C

7: 2-iodoxybenzoic acid / dimethylsulfoxide / 5 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo026817n