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

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Chemical Name:2(R)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-3(S)-(benzyloxy)-4(R)-hydroxy-2,3-dihydro-4H-pyran
CAS No.:138286-60-9
Molecular Formula:C₃₈H₄₁NO₇Si
Molecular Weight:651.832
Hs Code.:

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

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

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

There total 6 articles about 2(R)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-3(S)-(benzyloxy)-4(R)-hydroxy-2,3-dihydro-4H-pyran 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: 97.0%

: 122051-28-9
2(R)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-3(S)-(benzoyloxy)-2,3-dihydro-4H-pyran-4-one

: 138286-60-9
2(R)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-3(S)-(benzyloxy)-4(R)-hydroxy-2,3-dihydro-4H-pyran

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; ethanol; at -78 ℃; for 1h;
DOI:10.1021/jo00026a031

Reference yield:

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

: 138286-60-9
2(R)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-3(S)-(benzyloxy)-4(R)-hydroxy-2,3-dihydro-4H-pyran

Guidance literature:: Multi-step reaction with 4 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

4: 97 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; methanol / 1 h / -78 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; diisobutylaluminium hydride; trifluoroacetic acid; zinc dibromide; In methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00026a031

Reference yield:

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

: 138286-60-9
2(R)-<1'(S)-((Benzyloxycarbonyl)amino)-2'-((tert-butyldiphenylsilyl)oxy)ethyl>-3(S)-(benzyloxy)-4(R)-hydroxy-2,3-dihydro-4H-pyran

Guidance literature:: Multi-step reaction with 2 steps

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

2: 97 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; methanol / 1 h / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; trifluoroacetic acid; zinc dibromide; In methanol; ethanol;
DOI:10.1021/jo00026a031