(1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

Base Information

Chemical Name:(1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one
CAS No.:1519887-72-9
Molecular Formula:C₃₀H₃₉IO₄Si
Molecular Weight:618.627
Hs Code.:

(1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

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Chemical Property of (1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

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Technology Process of (1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

There total 10 articles about (1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-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: 4.0%

: 1519887-61-6
C₃₀H₄₀O₄Si

: 1519887-70-7
(1R,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

: 1519887-72-9
(1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

Guidance literature:: With iodine; sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 1.5h;
DOI:10.1021/jo402537u

Reference yield:

: 21378-21-2,54423-21-1
3-methylcyclohex-2-en-1-ol

: 1519887-70-7
(1R,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

: 1519887-72-9
(1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: vinyl n-butyrate / n-heptane

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 20 °C

2.2: 2 h / 0 °C

3.1: chloro-trimethyl-silane; lithium diisopropyl amide / tetrahydrofuran / 10 h / -78 - 20 °C

4.1: iodine; sodium hydrogencarbonate / acetonitrile / 1.5 h / 0 °C

With chloro-trimethyl-silane; oxalyl dichloride; vinyl n-butyrate; iodine; sodium hydrogencarbonate; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; acetonitrile;
DOI:10.1021/jo402537u

Reference yield:

: 18890-22-7,54423-21-1
(R)-3-methylcyclohex-2-en-1-ol

: 1519887-70-7
(1R,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

: 1519887-72-9
(1S,3S,5R,3a'S,4'S,7a'S)-3-[(tert-butyldiphenylsilyl)-oxymethyl ]4'-iodo-5,7a'-dimethyl-2,3'-dioxaspiro[cyclopentane-1,1'-hexahydroindan]-2'-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 20 °C

1.2: 2 h / 0 °C

2.1: chloro-trimethyl-silane; lithium diisopropyl amide / tetrahydrofuran / 10 h / -78 - 20 °C

3.1: iodine; sodium hydrogencarbonate / acetonitrile / 1.5 h / 0 °C

With chloro-trimethyl-silane; oxalyl dichloride; iodine; sodium hydrogencarbonate; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo402537u