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

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Chemical Name:(2S,3S)-methyl 3-(((3aR,4S,6R,6aR)-6-(azidomethyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-2-(((benzyloxy)carbonyl)amino)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoate
CAS No.:1612257-25-6
Molecular Formula:C₄₈H₇₈N₆O₁₃Si₂
Molecular Weight:1003.35
Hs Code.:

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

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

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

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

There total 4 articles about (2S,3S)-methyl 3-(((3aR,4S,6R,6aR)-6-(azidomethyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-2-(((benzyloxy)carbonyl)amino)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoate 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: 72.0%

: C₁₀H₁₆FN₃O₃

: 1612257-24-5
(2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)-3-hydroxypropanoate

: 1612257-25-6
(2S,3S)-methyl 3-(((3aR,4S,6R,6aR)-6-(azidomethyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-2-(((benzyloxy)carbonyl)amino)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoate

Guidance literature:: C₁₀H₁₆FN₃O₃; (2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)-3-hydroxypropanoate; In dichloromethane; at -30 ℃; for 0.25h; Molecular sieve;

With boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 36h; Molecular sieve;
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

: 1612257-25-6
(2S,3S)-methyl 3-(((3aR,4S,6R,6aR)-6-(azidomethyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-2-(((benzyloxy)carbonyl)amino)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoate

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: (4S,5S)-methyl 5-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)-4,5-dihydrooxazole-4-carboxylate

: 1612257-25-6
(2S,3S)-methyl 3-(((3aR,4S,6R,6aR)-6-(azidomethyl)-2,2-diethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)oxy)-2-(((benzyloxy)carbonyl)amino)-3-((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-bis((triisopropylsilyl)oxy)tetrahydrofuran-2-yl)propanoate

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

3.2: 36 h / -30 °C / Molecular sieve

With hydrogenchloride; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol501397b