(1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate

Base Information

Chemical Name:(1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate
CAS No.:1448722-44-8
Molecular Formula:C₂₄H₃₁N₃O₅
Molecular Weight:441.527
Hs Code.:

Synonyms:(1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate

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Chemical Property of (1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate

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Technology Process of (1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate

There total 4 articles about (1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-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: 94.0%

: 623-73-4
diazoacetic acid ethyl ester

: 240129-05-9
(1S,3R,4aS,7R,8aR)-benzyl 3-methyl-6-oxodecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate

: 1448722-44-8
(1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 5.08333h; Inert atmosphere;
DOI:10.1021/ol401954f

Reference yield:

: 1448722-43-7
(1S,3R,4aS,7R,8aR)-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one

: 1448722-44-8
(1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: potassium carbonate / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

2: lithium diisopropyl amide / hexane; tetrahydrofuran / 5.08 h / -78 °C / Inert atmosphere

With potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol401954f

Reference yield:

: 1448722-42-6
(1S,3R,4aS,7R,8aR)-10-benzyl-3-methyloctahydro-1,7-(epiminomethano)naphthalen-6(2H)-one

: 1448722-44-8
(1S,3R,4aS,6R,7R,8aR)-benzyl 6-(1-diazo-2-ethoxy-2-oxoethyl)-6-hydroxy-3-methyldecahydro-1,7-(epiminomethano)naphthalene-10-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 22 h / 20 °C / Inert atmosphere

2: potassium carbonate / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

3: lithium diisopropyl amide / hexane; tetrahydrofuran / 5.08 h / -78 °C / Inert atmosphere

With 10 wt% Pd(OH)2 on carbon; hydrogen; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol401954f