benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate

Base Information

Chemical Name:benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate
CAS No.:890649-00-0
Molecular Formula:C₂₄H₃₉NO₈Si
Molecular Weight:497.661
Hs Code.:

Synonyms:benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate

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Chemical Property of benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate

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Technology Process of benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate

There total 8 articles about benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate 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: 67.0%

: 890649-01-1
benzyl [(E)-(S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-4-oxo-hex-2-enyl]carbamate

: 890649-00-0
benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate

Guidance literature:: With methanesulfonamide; AD-mix-β; sodium hydrogencarbonate; potassium osmate(VI); In water; tert-butyl alcohol; at 20 ℃; for 18h;
DOI:10.1002/ejoc.200500914

Reference yield:

: 18742-02-4
2-bromo-2-(2-ethyl)dioxolane

: 890649-00-0
benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-BuLi / tetrahydrofuran; hexane / 1 h / -35 °C

1.2: tetrahydrofuran; hexane / 3 h / -35 - 0 °C

1.3: 34 percent / aq. HCl / tetrahydrofuran; hexane / 0.17 h / 0 °C

2.1: 73 percent / Hoveyda-Blechert ruthenium catalyst / CH₂Cl₂ / 72 h / Heating

3.1: 67 percent / AD-Mix-β; NaHCO3; MeSO2NH2 / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 18 h / 20 °C

With n-butyllithium; Hoveyda-Grubbs catalyst second generation; methanesulfonamide; AD-mix-β; sodium hydrogencarbonate; potassium osmate(VI); In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1002/ejoc.200500914

Reference yield:

: 75266-40-9
N-benzyloxycarbonyl-L-α-vinylglycine methyl ester

: 890649-00-0
benzyl [(1R,2R,3S)-1-(tert-butyldimethylsilanyloxymethyl)-6-(1,3-dioxolan-2-yl)-2,3-dihydroxy-4-oxo-hexyl]carbamate

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / LiBH₄ / methanol; diethyl ether / 2 h / 20 °C

2: 88 percent / imidazole / dimethylformamide / 18 h / 20 °C

3: 73 percent / Hoveyda-Blechert ruthenium catalyst / CH₂Cl₂ / 72 h / Heating

4: 67 percent / AD-Mix-β; NaHCO3; MeSO2NH2 / K2OsO4*2H2O / 2-methyl-propan-2-ol; H2O / 18 h / 20 °C

With 1H-imidazole; lithium borohydride; Hoveyda-Grubbs catalyst second generation; methanesulfonamide; AD-mix-β; sodium hydrogencarbonate; potassium osmate(VI); In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/ejoc.200500914