(3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one

Base Information

Chemical Name:(3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one
CAS No.:533924-09-3
Molecular Formula:C₂₃H₃₅IO₃SSi
Molecular Weight:546.585
Hs Code.:

Synonyms:(3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one

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Chemical Property of (3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one

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Technology Process of (3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one

There total 6 articles about (3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-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: 79.0%

: 184435-75-4
(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

: 533924-08-2
(EZ,R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl trifluoromethanesulfonate

: 533924-09-3
(3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one

Guidance literature:: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one; With potassium hexamethylsilazane; In tetrahydrofuran; at 0 ℃;

(EZ,R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl trifluoromethanesulfonate; In tetrahydrofuran; at 20 ℃; Further stages.;
DOI:10.1021/ol006938e

Reference yield: 79.0%

: 184435-75-4
(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

: 533924-08-2
(EZ,R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl trifluoromethanesulfonate

: 533924-09-3
(3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one

: (5R)-5-(tert-butyldimethylsilyloxy)-1-iodo-6-phenylsulfenyl-1-hexene

Guidance literature:: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 0 ℃; for 0.0833333h;

(EZ,R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl trifluoromethanesulfonate; In tetrahydrofuran; toluene; at 20 ℃; for 2h;
DOI:10.1002/chem.200390040

Reference yield:

: (EZ,R)-6-iodo-5-hexene-1,2-diol

: 533924-09-3
(3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / -50 °C

2.1: 243 mg / CH₂Cl₂ / 0.08 h / 0 °C

3.1: KHMDS / toluene; tetrahydrofuran / 0.08 h / 0 °C

3.2: 79 percent / toluene; tetrahydrofuran / 2 h / 20 °C

With 2,6-dimethylpyridine; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/chem.200390040