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

Base Information

Chemical Name:benzyl (3aR,5R,6R,6aR)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl(prop-2-ynyl)carbamate
CAS No.:1620809-01-9
Molecular Formula:C₂₀H₂₃NO₅
Molecular Weight:357.406
Hs Code.:

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

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

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

There total 1 articles about benzyl (3aR,5R,6R,6aR)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl(prop-2-ynyl)carbamate 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: 93.0%

: 910479-44-6
((3aR,5R,6R,6aR)-2,2-Dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-carbamic acid benzyl ester

: 106-96-7
propargyl bromide

: 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

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1002/ejoc.201402142

Reference yield: 82.0%

: 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

: 1620809-02-0
C₂₀H₂₃NO₅

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; ethene; In dichloromethane; at 20 ℃; for 10 - 12h; under 760.051 Torr; 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

: C₁₆H₂₃NO₈

Guidance literature:: Multi-step reaction with 10 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

4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide; water / acetone; tert-butyl alcohol / 4 h / 20 °C / Inert atmosphere

5.1: sodium periodate / methanol; water / 0.92 - 1 h / 0 °C / Inert atmosphere

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

7.1: triethylamine; dmap / dichloromethane / 10 - 12 h / 20 °C / Inert atmosphere

8.1: water; sodium periodate; ruthenium(III) chloride trihydrate / ethyl acetate / 0.5 h / 0 °C / Inert atmosphere

9.1: triethylamine; dmap / dichloromethane / 10 - 12 h / 20 °C / Inert atmosphere

10.1: methanol; sodium methylate / 0 - 20 °C / Inert atmosphere

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