2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one

Base Information

Chemical Name:2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one
CAS No.:127896-80-4
Molecular Formula:C₃₁H₃₅NO₅Si
Molecular Weight:529.708
Hs Code.:

Synonyms:2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one

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Chemical Property of 2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one

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Technology Process of 2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one

There total 4 articles about 2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one 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: 86.0%

: 73431-56-8
trans-1-ethoxy-3-<(trimethylsilyl)oxy>-buta-1,3-diene

: 122051-27-8
N-(Benzyloxycarbonyl)-O-(tert-butyldiphenylsilyl)-L-serinal

: 127896-80-4
2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one

Guidance literature:: With zinc dibromide; In tetrahydrofuran; for 48h; Ambient temperature;
DOI:10.1016/S0040-4039(01)93434-3

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 127896-80-4
2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / imidazole / dimethylformamide

2: 70 percent / DIBAL / diethyl ether; toluene / 1 h / temperature below -70 deg C

3: 1. ZnBr₂, 2. trifluoroacetic acid (TFA) / 1. THF, r.t., overnight; 2. CH₂Cl₂, 5 min

With 1H-imidazole; diisobutylaluminium hydride; trifluoroacetic acid; zinc dibromide; In diethyl ether; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00026a031

Reference yield:

: 135245-97-5
methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(phenylmethoxy)carbonylamino]propanoate

: 127896-80-4
2(S)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-2,3-dihydro-4H-pyran-4-one

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / DIBAL / diethyl ether; toluene / 1 h / temperature below -70 deg C

2: 1. ZnBr₂, 2. trifluoroacetic acid (TFA) / 1. THF, r.t., overnight; 2. CH₂Cl₂, 5 min

With diisobutylaluminium hydride; trifluoroacetic acid; zinc dibromide; In diethyl ether; toluene;
DOI:10.1021/jo00026a031