(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

Base Information

Chemical Name:(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one
CAS No.:356059-97-7
Molecular Formula:C₂₁H₂₃IO₄
Molecular Weight:466.316
Hs Code.:

Synonyms:(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

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Chemical Property of (1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

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Technology Process of (1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

There total 20 articles about (1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-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: 89.0%

: C₂₁H₂₂O₄

: 356059-97-7
(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

Guidance literature:: With trimethylsilyl iodide; In tetrachloromethane; at -10 ℃;
DOI:10.1016/S0040-4039(00)01312-5

Reference yield: 89.0%

: 313548-03-7
(1R,2S,4S,5S,6R,7R,8R,9S,10S)-4-benzyl-6,9-epoxy-4,5-(O-isopropylidenedioxy)tetracyclo[6.2.1.0^2,7.0^2,10]undecan-3-one

: 356059-97-7
(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

Guidance literature:: With trimethylsilyl iodide; In tetrachloromethane; at -10 ℃; for 3h;
DOI:10.1016/j.tet.2005.10.082

Reference yield:

: C₂₁H₂₂O₅

: 356059-97-7
(1S,2S,3S,4R,4aR,5R,6S,7S,8aR)-7-benzyl-3,5-epoxy-2-iodo-6,7-O-isopropylidenedioxy-1,2,3,4,4a,5,6,8a-octahydro-endo-1,4-methanonaphthalen-8-one

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / DMAP / acetonitrile / 25 °C

2: 79 percent / n-Bu₃SnH / AIBN / toluene / 110 °C

3: 89 percent / TMSI / CCl₄ / -10 °C

With dmap; trimethylsilyl iodide; tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; toluene; acetonitrile; 1: Acylation / 2: Reduction / 3: Iodination;
DOI:10.1016/S0040-4039(00)01312-5