(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester
CAS No.:325700-26-3
Molecular Formula:C₂₉H₃₈N₂O₈Si
Molecular Weight:570.715
Hs Code.:

Synonyms:(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

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Chemical Property of (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

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Technology Process of (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

There total 9 articles about (2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 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: 84.0%

: 325699-99-8
(2R,3R)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

: 62-23-7
4-nitro-benzoic acid

: 325700-26-3
(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 0.5h;
DOI:10.1021/ol006907j

Reference yield:

: 98-01-1
furfural

: 325700-26-3
(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: Mg / diethyl ether / 1 h / Heating

1.2: 90 percent / diethyl ether / 12 h

2.1: aq. HCl / diethyl ether / 1 h

3.1: OsO₄; (DHQ)2PHAL / diethyl ether; 2-methyl-propan-2-ol; H₂O / 1 h / 25 °C

3.2: 3.71 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 23 °C

4.1: 87 percent / m-CPBA / CH₂Cl₂ / 3 h

5.1: 87 percent / TsOH / CH₂Cl₂ / 24 h

6.1: 86 percent / NaBH₄; CeCl₃ / methanol; CH₂Cl₂ / 2 h / -78 °C

7.1: 84 percent / PPh₃; DEAD / tetrahydrofuran / 0.5 h

With hydrogenchloride; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; Hydroquinone 1,4-phthalazinediyl diether; toluene-4-sulfonic acid; magnesium; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 1.2: Grignard reaction / 6.1: Luche reduction / 7.1: Mitsunobu inversion;
DOI:10.1021/ol006907j

Reference yield:

: 1487-18-9
(furan-2-yl)ethylene

: 325700-26-3
(2R,3S)-2-(tert-butyldimethylsilyloxymethyl)-6-ethoxy-3-(4-nitro-benzoyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: OsO₄; (DHQ)2PHAL / diethyl ether; 2-methyl-propan-2-ol; H₂O / 1 h / 25 °C

1.2: 3.71 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 23 °C

2.1: 87 percent / m-CPBA / CH₂Cl₂ / 3 h

3.1: 87 percent / TsOH / CH₂Cl₂ / 24 h

4.1: 86 percent / NaBH₄; CeCl₃ / methanol; CH₂Cl₂ / 2 h / -78 °C

5.1: 84 percent / PPh₃; DEAD / tetrahydrofuran / 0.5 h

With sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; Hydroquinone 1,4-phthalazinediyl diether; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 4.1: Luche reduction / 5.1: Mitsunobu inversion;
DOI:10.1021/ol006907j