(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione

Base Information

Chemical Name:(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione
CAS No.:171625-75-5
Molecular Formula:C₄₀H₅₄O₁₁
Molecular Weight:710.862
Hs Code.:

(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione

Synonyms:(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione

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Chemical Property of (2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione

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Technology Process of (2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione

There total 4 articles about (2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione 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:

: 3587-60-8
Benzyloxymethyl chloride

: 171625-75-5
(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / Bu₄N⁽¹⁺⁾*I^(1-), (i-Pr)2NEt / dimethylformamide / 1.) room temp., overnight, 2.) 50 deg C, 1 h

2: 75 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 0.5 h / Ambient temperature

3: 1.) (COCl)2, DMSO, 2.) (i-Pr)2NEt / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) -78 deg C, 1 h; -78 deg C to 0 deg C, 1 h

With oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo00129a027

Reference yield:

: 171625-73-3
(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-11'-(tert-Butyldimethylsiloxy)dodecahydro-4',10'-dihydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(5'H)-[7,10]methanobenzocyclodecen)-5'-one

: 171625-75-5
(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / Bu₄N⁽¹⁺⁾*I^(1-), (i-Pr)2NEt / dimethylformamide / 1.) room temp., overnight, 2.) 50 deg C, 1 h

2: 75 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 0.5 h / Ambient temperature

3: 1.) (COCl)2, DMSO, 2.) (i-Pr)2NEt / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) -78 deg C, 1 h; -78 deg C to 0 deg C, 1 h

With oxalyl dichloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo00129a027

Reference yield:

: 171625-80-2
(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]-11'-(tert-butyldimethylsiloxy)dodecahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(5'H)-[7,10]methanobenzocyclodec...)

: 171625-75-5
(2'R,4S,4'S,4'aS,6'R,7'S,10'S,11'S,12'aS)-4'-[(Benzyloxy)methoxy]octahydro-10'-hydroxy-2'-[(p-methoxybenzyl)oxy]-6'-(methoxymethoxy)-2,2,4'a,13',13'-pentamethylspiro(1,3-dioxolane-4,1'(2'H)-[7,10]methanobenzocyclodecene)-5',11'(3'H,6'H)-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 0.5 h / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) (i-Pr)2NEt / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) -78 deg C, 1 h; -78 deg C to 0 deg C, 1 h

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1021/jo00129a027