ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate

Base Information

Chemical Name:ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate
CAS No.:489442-10-6
Molecular Formula:C₂₈H₄₀O₇S₂Si
Molecular Weight:580.839
Hs Code.:

Synonyms:ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate

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Chemical Property of ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate

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Technology Process of ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate

There total 7 articles about ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate 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: 80.0%

: 489441-69-2
2-(tert-butyl-dimethyl-silanyloxymethyl)-6-phenylsulfanyl-5-phenylsulfanylmethyl-hex-3-enoic acid ethyl ester

: 489442-10-6
ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate

Guidance literature:: With sodium tungstate; dihydrogen peroxide; In methanol; at 20 ℃; for 18h;
DOI:10.1021/ol0271436

Reference yield:

: 55387-85-4
3-hydroxymethyl-4-hydroxybutanal diethyl acetal

: 489442-10-6
ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tributylphosphine / tetrahydrofuran / 0.17 h / 0 °C

1.2: 93 percent / tetrahydrofuran / 3 h / 20 °C

2.1: 88 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C

3.1: 81 percent / CH₂Cl₂ / 20 °C

4.1: LHMDS; HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

4.3: 97 percent / N,N-diisopropylamine / CH₂Cl₂ / 0.25 h / 20 °C

5.1: 80 percent / sodium tungstate; hydrogen peroxide / methanol / 18 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tungstate; tributylphosphine; dihydrogen peroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; 3.1: Horner-Emmons-Wittig reaction;
DOI:10.1021/ol0271436

Reference yield:

: 14204-27-4
N-phenylthiophthalimide

: 489442-10-6
ethyl (3E)-2-({tert-butyl(dimethyl)silyloxy}methyl)-6-(phenylsulfonyl)-5-[(phenylsulfonyl)methyl]hex-3-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tributylphosphine / tetrahydrofuran / 0.17 h / 0 °C

1.2: 93 percent / tetrahydrofuran / 3 h / 20 °C

2.1: 88 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C

3.1: 81 percent / CH₂Cl₂ / 20 °C

4.1: LHMDS; HMPA / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

4.3: 97 percent / N,N-diisopropylamine / CH₂Cl₂ / 0.25 h / 20 °C

5.1: 80 percent / sodium tungstate; hydrogen peroxide / methanol / 18 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tungstate; tributylphosphine; dihydrogen peroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; 3.1: Horner-Emmons-Wittig reaction;
DOI:10.1021/ol0271436