methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate

Base Information

Chemical Name:methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate
CAS No.:404369-29-5
Molecular Formula:C₃₁H₃₉NO₄Si
Molecular Weight:517.74
Hs Code.:

Synonyms:methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate

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Chemical Property of methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate

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Technology Process of methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate

There total 5 articles about methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate 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: 78.0%

: 404369-28-4
methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

: 404369-29-5
methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate

Guidance literature:: methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 10h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran;
DOI:10.1016/S0040-4020(01)01070-5

Reference yield:

: 302593-20-0
methyl 2-deoxy-3,4-O-isopropylidene-5-O-methanesulfonyl-2-[(9-phenyl-9-fluorenyl)-amino]-D-arabinonate

: 404369-29-5
methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / LiI / dimethylformamide / 80 °C

2.1: 90 percent / n-BuLi / tetrahydrofuran / 0.33 h / -40 °C

3.1: 98 percent / imidazole / dimethylformamide / 12 h / 20 °C

4.1: BH₃*SMe₂ / tetrahydrofuran / 10 h / 20 °C

4.2: 78 percent / NaOH; aq. H₂O₂ / tetrahydrofuran

With 1H-imidazole; n-butyllithium; dimethylsulfide borane complex; lithium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01070-5

Reference yield:

: 302593-18-6
methyl 2-deoxy-3,4-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-arabinonate

: 404369-29-5
methyl (2R,3S)-3-(tert-butyldimethylsilyl)oxy-5-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / Et₃N / tetrahydrofuran / 0.25 h / 20 °C

2.1: 90 percent / LiI / dimethylformamide / 80 °C

3.1: 90 percent / n-BuLi / tetrahydrofuran / 0.33 h / -40 °C

4.1: 98 percent / imidazole / dimethylformamide / 12 h / 20 °C

5.1: BH₃*SMe₂ / tetrahydrofuran / 10 h / 20 °C

5.2: 78 percent / NaOH; aq. H₂O₂ / tetrahydrofuran

With 1H-imidazole; n-butyllithium; dimethylsulfide borane complex; triethylamine; lithium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01070-5