ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate

Base Information

Chemical Name:ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate
CAS No.:552302-58-6
Molecular Formula:C₂₇H₃₉NO₆Si
Molecular Weight:501.695
Hs Code.:

Synonyms:ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate

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Chemical Property of ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate

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Technology Process of ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate

There total 9 articles about ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate 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:

: 60656-87-3
benzyloxyacetoaldehyde

: 552302-58-6
ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / KOH / methanol / 1.5 h / 20 °C

2: 82 percent / MsCl; DMAP; Et₃N / CH₂Cl₂ / 1 h / 20 °C

3: 53 percent / BuLi / tetrahydrofuran; hexane / 4 h / -78 - 14 °C

4: dimethylformamide; CH₂Cl₂ / 7.5 h / 0 °C

With dmap; potassium hydroxide; n-butyllithium; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200390063

Reference yield:

: 40435-14-1
(S)-1-phenyl-2-(tosyloxy)ethanol

: 552302-58-6
ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate

Guidance literature:: Multi-step reaction with 7 steps

1: 39.5 percent / KCN; DMAP / methanol / 23 h / 20 °C

2: 57.4 percent / aq. NaOH; H₂O₂ / 6.5 h / 20 °C

3: 69 percent / Et₃N / CH₂Cl₂ / 120 h / 20 °C

4: 75 percent / Me₃Si-triflate / CH₂Cl₂ / 7 h / -70 °C

5: 86 percent / BuLi / hexane; tetrahydrofuran / 0.75 h / -75 °C

6: 69 percent / H₂SO₄ / 17 h / Heating

7: dimethylformamide; CH₂Cl₂ / 7.5 h / 0 °C

With dmap; potassium cyanide; sodium hydroxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; dihydrogen peroxide; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200390063

Reference yield:

: 194807-63-1
(E)-(((3-nitroallyl)oxy)methyl)benzene

: 552302-58-6
ethyl (-)-(2S,3S)-4-(benzyloxy)-2-[(R)-{[(tert-butyl)dimethylsilyl]oxy}(phenyl)methyl]-3-(nitromethyl)butanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 53 percent / BuLi / tetrahydrofuran; hexane / 4 h / -78 - 14 °C

2: dimethylformamide; CH₂Cl₂ / 7.5 h / 0 °C

With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200390063