(R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate

Base Information

• Chemical Name: (R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate
• CAS No.: 1620809-03-1
• Molecular Formula: C₂₃H₂₇NO₈
• Molecular Weight: 445.469

Synonyms:(R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate

Chemical Property of (R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate

There total 4 articles about (R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate 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:

C17H21NO5 (1620809-05-3) + acetic anhydride (108-24-7) → (R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate (1620809-03-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.201402142

Reference yield:

benzyl (3aR,5R,6R,6aR)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl(prop-2-ynyl)carbamate (1620809-01-9) → (R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate (1620809-03-1)

Guidance literature:

Multi-step reaction with 3 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: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; ethene; sulfuric acid; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.201402142

Reference yield:

((3aR,5R,6R,6aR)-2,2-Dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-carbamic acid benzyl ester (910479-44-6) → (R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-vinyl-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate (1620809-03-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere

2.1: 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

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

3.2: 0 - 20 °C / Inert atmosphere

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

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; ethene; sulfuric acid; sodium hydride; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/ejoc.201402142

upstream raw materials:

C₁₇H₂₁NO₅

acetic anhydride

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

((3aR,5R,6R,6aR)-2,2-Dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-carbamic acid benzyl ester

Downstream raw materials:

(R)-1-[(2R,3R)-3-acetoxy-1-(benzyloxycarbonyl)-5-(1,2-dihydroxyethyl)-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate

(R)-1-[(2R,3R)-3-acetoxy-5-(acetoxymethyl)-1-(benzyloxycarbonyl)-1,2,3,6-tetrahydropyridin-2-yl]ethane-1,2-diyl diacetate

C₂₂H₂₅NO₉

(2S,3S,4S,5S)-5-(acetoxymethyl)-1-(benzyloxycarbonyl)-2-[(R)-1,2-bis(acetoxyethyl)]piperidine-3,4,5-triyl triacetate

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