(2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid

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Chemical Name:(2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid
CAS No.:1612257-27-8
Molecular Formula:C₅₂H₈₆N₄O₁₅Si₂
Molecular Weight:1063.44
Hs Code.:

(2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid

Synonyms:(2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid

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Chemical Property of (2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid

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Technology Process of (2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid

There total 7 articles about (2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid 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: 64.0%

: 1612257-26-7
(2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoate

: 1612257-27-8
(2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid

Guidance literature:: With lithium iodide; In ethyl acetate; at 80 ℃; for 20h;
DOI:10.1021/ol501397b

Reference yield:

: 2',3'-O-bis(triisopropylsilyl)uridine

: 1612257-27-8
(2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: dicyclohexyl-carbodiimide; trifluoroacetic acid; pyridine / toluene; dimethyl sulfoxide / 20 h / 0 - 5 °C

2.1: copper(l) chloride; triphenylphosphine; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / 20 °C

3.1: hydrogenchloride / tetrahydrofuran / 24 h / 20 °C

4.1: sodium hydrogencarbonate / water; tetrahydrofuran / 20 h / 0 °C

5.1: dichloromethane / 0.25 h / -30 °C / Molecular sieve

5.2: 36 h / -30 °C / Molecular sieve

6.1: triphenylphosphine / water; tetrahydrofuran; toluene / 18 h / 50 °C

6.2: 5 h / 50 °C

7.1: lithium iodide / ethyl acetate / 20 h / 80 °C

With pyridine; hydrogenchloride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; copper(l) chloride; lithium iodide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1021/ol501397b

Reference yield:

: 1612257-21-2
(2S,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-carbaldehyde

: 1612257-27-8
(2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-(((3aR,4S,6R,6aR)-6-(((tert-butoxycarbonyl)amino)methyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: copper(l) chloride; triphenylphosphine; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / 20 °C

2.1: hydrogenchloride / tetrahydrofuran / 24 h / 20 °C

3.1: sodium hydrogencarbonate / water; tetrahydrofuran / 20 h / 0 °C

4.1: dichloromethane / 0.25 h / -30 °C / Molecular sieve

4.2: 36 h / -30 °C / Molecular sieve

5.1: triphenylphosphine / water; tetrahydrofuran; toluene / 18 h / 50 °C

5.2: 5 h / 50 °C

6.1: lithium iodide / ethyl acetate / 20 h / 80 °C

With hydrogenchloride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(l) chloride; lithium iodide; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1021/ol501397b