(4aS,5S)-5-benzyloxymethoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Base Information

Chemical Name:(4aS,5S)-5-benzyloxymethoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
CAS No.:1373344-25-2
Molecular Formula:C₁₉H₂₄O₃
Molecular Weight:300.398
Hs Code.:

Synonyms:(4aS,5S)-5-benzyloxymethoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

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Chemical Property of (4aS,5S)-5-benzyloxymethoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

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Technology Process of (4aS,5S)-5-benzyloxymethoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

There total 2 articles about (4aS,5S)-5-benzyloxymethoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-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: 78.0%

: 3587-60-8
Benzyloxymethyl chloride

: 878-47-7,4242-00-6,34996-06-0,50302-16-4,70191-02-5,34996-05-9
(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one

: 1373344-25-2
(4aS,5S)-5-benzyloxymethoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1135/cccc2011039

Reference yield:

: 20007-99-2,33878-99-8,100348-93-4,20007-72-1
Wieland-Miescher ketone

: 1373344-25-2
(4aS,5S)-5-benzyloxymethoxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: sodium tetrahydroborate; (R,R)-TADDOL / methanol; dichloromethane / 0.25 h / -78 °C / Inert atmosphere

2: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h / 20 °C

With sodium tetrahydroborate; (R,R)-TADDOL; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;
DOI:10.1135/cccc2011039