(6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one

Base Information

Chemical Name:(6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one
CAS No.:1443533-69-4
Molecular Formula:C₂₇H₃₆N₂O₅S
Molecular Weight:500.659
Hs Code.:

(6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one

Synonyms:(6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one

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Chemical Property of (6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one

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Technology Process of (6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one

There total 3 articles about (6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one 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: 52.0%

: (4aR,5S,6S,6aR,9S,11aS,11bS,14R)-2-bromo-5,6,14-trihydroxy-4,4-dimethyl-8-methylenedecahydro-1H-6,11b-(epoxymethano)-6a,9-methanocyclohepta[a]naphthalene-1,7(8H)-dione

: 5055-72-1
N-cyclohexylthiourea

: 1443533-69-4
(6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one

Guidance literature:: In ethanol; at 20 ℃; Reflux; Inert atmosphere;
DOI:10.1021/jm400367n

Reference yield:

: 28957-04-2,28957-10-0
oridonin

: 1443533-69-4
(6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: Jones reagent / acetone / 0 - 20 °C / Inert atmosphere

2: pyridinium hydrobromide perbromide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3: ethanol / 20 °C / Reflux; Inert atmosphere

With Jones reagent; pyridinium hydrobromide perbromide; In tetrahydrofuran; ethanol; acetone; 3: |Hantzsch Thiazole Synthesis;
DOI:10.1021/jm400367n

Reference yield:

: 29288-74-2
(4aR,5S,6S,6aR,9S,11aS,11bS,14R)-5,6,14-trihydroxy-4,4-dimethyl-8-methylenedecahydro-1H-6,11b-(epoxymethano)-6a,9-methanocyclohepta[a]naphthalene-1,7(8H)-dione

: 1443533-69-4
(6S,7S,7aR,10R,12bR,15R)-2-(cyclohexylamino)-6,7,15-trihydroxy-5,5-dimethyl-9-methylene-5,5a,6,7,10,11,12,12a-octahydro-4H-7,12b-(epoxymethano)-7a,10-methanocyclohepta-[7,8]naphtho[1,2-d]thiazol-8(9H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium hydrobromide perbromide / tetrahydrofuran / 4 h / 20 °C

2: ethanol / 3 h / Reflux

With pyridinium hydrobromide perbromide; In tetrahydrofuran; ethanol;