(S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

Base Information

Chemical Name:(S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide
CAS No.:1374036-13-1
Molecular Formula:C₃₁H₄₆FNO₂SSi
Molecular Weight:543.862
Hs Code.:

Synonyms:(S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

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Chemical Property of (S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

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Technology Process of (S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

There total 5 articles about (S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide 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:

: 1374036-12-0
(R,E)-N-((Z)-2-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-2-fluoroethylidene)-2-methylpropane-2-sulfinamide

: 1888-75-1
isopropyllithium

: 1374036-13-1
(S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

: (S)-N-((R,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

Guidance literature:: In toluene; pentane; at -78 ℃; for 1h; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.bmcl.2012.02.051

Reference yield:

: (Z)-2-(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-2-fluoroacetaldehyde

: 1374036-13-1
(S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

: (S)-N-((R,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

Guidance literature:: Multi-step reaction with 2 steps

1: titanium(IV) tetraethanolate / tetrahydrofuran; isopropyl alcohol / 4 h / 20 °C

2: toluene; pentane / 1 h / -78 °C

With titanium(IV) tetraethanolate; In tetrahydrofuran; isopropyl alcohol; toluene; pentane;
DOI:10.1016/j.bmcl.2012.02.051

Reference yield:

: 130733-88-9
2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentan-1-one

: 1374036-13-1
(S)-N-((S,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

: (S)-N-((R,Z)-1-((R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopentylidene)-1-fluoro-3-methylbutan-2-yl)-2-methylpropane-2-sulfinamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

1.2: -78 - 20 °C

2.1: diisobutylaluminium hydride / hexane; toluene / 4 h / 0 °C

3.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C

4.1: titanium(IV) tetraethanolate / tetrahydrofuran; isopropyl alcohol / 4 h / 20 °C

5.1: toluene; pentane / 1 h / -78 °C

With titanium(IV) tetraethanolate; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; isopropyl alcohol; toluene; mineral oil; pentane; 1.1: Horner-Emmons reaction / 1.2: Horner-Emmons reaction / 3.1: Dess-Martin oxidation;
DOI:10.1016/j.bmcl.2012.02.051