benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Base Information

Chemical Name:benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate
CAS No.:1620809-14-4
Molecular Formula:C₂₀H₂₅NO₈
Molecular Weight:407.42
Hs Code.:

Synonyms:benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate

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Chemical Property of benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate

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Technology Process of benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate

There total 7 articles about benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate 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: 81.0%

: 1620809-12-2
benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-vinyl-5,6-dihydropyridine-1(2H)-carboxylate

: 1620809-14-4
benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; tert-butyl alcohol; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1002/ejoc.201402142

Reference yield:

: 1620809-01-9
benzyl (3aR,5R,6R,6aR)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl(prop-2-ynyl)carbamate

: 1620809-14-4
benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; ethene / dichloromethane / 10 - 12 h / 20 °C / 760.05 Torr / Inert atmosphere

2.1: sulfuric acid / acetonitrile; water / 6 h / 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: sodium periodate / methanol; water / 0.67 h / 0 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C / Inert atmosphere

5.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone; tert-butyl alcohol / 4 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; ethene; sulfuric acid; water; 4-methylmorpholine N-oxide; triethylamine; In methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1002/ejoc.201402142

Reference yield:

: C₁₆H₁₇NO₄

: 1620809-14-4
benzyl (5R,6S)-5-acetoxy-6-(acetoxymethyl)-3-(1,2-dihydroxyethyl)-5,6-dihydropyridine-1(2H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

3: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone; tert-butyl alcohol / 4 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; triethylamine; In methanol; dichloromethane; acetone; tert-butyl alcohol;
DOI:10.1002/ejoc.201402142