(-)-(S_S,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol

Base Information

• Chemical Name: (-)-(S_S,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol
• CAS No.: 177933-24-3
• Molecular Formula: C₃₃H₆₁NO₄SSi₂
• Molecular Weight: 624.089

Synonyms:(-)-(S_S,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol

Chemical Property of (-)-(S_S,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol

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Technology Process of (-)-(S_S,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol

There total 4 articles about (-)-(S_S,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol 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:

(2S,4R)-4-Isopropyl-2-p-tolyl-4H,5H-2λ4-[1,2,3]oxathiazole 2-oxide (170900-87-5) → (-)-(SS,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol (177933-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran; diethyl ether / -78 °C

2: EtMe₂N, DMAP / CH₂Cl₂ / 18 h

3: 1.) n-BuLi, 3.) trimethylsilyl triflate, 4.) n-BuLi

4: 1.) n-BuLi, 2.) ClTi(OiPr)3, 4.) aq. (NH₄)2CO₃

With triisopropoxytitanium(IV) chloride; dmap; n-butyllithium; N,N-dimethyl-ethanamine; trimethylsilyl trifluoromethanesulfonate; ammonium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja9530735

Reference yield:

C13H21NO2S → (-)-(SS,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol (177933-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1: EtMe₂N, DMAP / CH₂Cl₂ / 18 h

2: 1.) n-BuLi, 3.) trimethylsilyl triflate, 4.) n-BuLi

3: 1.) n-BuLi, 2.) ClTi(OiPr)3, 4.) aq. (NH₄)2CO₃

With triisopropoxytitanium(IV) chloride; dmap; n-butyllithium; N,N-dimethyl-ethanamine; trimethylsilyl trifluoromethanesulfonate; ammonium carbonate; In dichloromethane;

DOI:10.1021/ja9530735

Reference yield:

(2R)-2-(tert-butyldimethylsilyloxy)propanal (74262-56-9,87727-28-4,104501-60-2,111819-71-7) + (+)-(SS)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-S-(cyclopent-1-en-1-ylmethyl)-S-(4-methylphenyl)sulfoximide (177796-05-3) → (-)-(SS,N(1R),1R,1'R,2R,2'Z)-1-(2'-{[N-(1-{[(tert-butyldimethylsilyl)oxy]methyl}-2-methylpropyl)-S-4-(methylphenyl)sulfonimidoyl]methylene}cyclopent-1'-yl)-2-[(tert-butyldimethylsilyl)oxy]propan-1-ol (177933-24-3)

Guidance literature:

With triisopropoxytitanium(IV) chloride; n-butyllithium; ammonium carbonate; Yield given. Multistep reaction;

DOI:10.1021/ja9530735

upstream raw materials:

(2R)-2-(tert-butyldimethylsilyloxy)propanal

(+)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-S-(cyclopent-1-en-1-ylmethyl)-S-(4-methylphenyl)sulfoximide

(2S,4R)-4-Isopropyl-2-p-tolyl-4H,5H-2λ⁴-[1,2,3]oxathiazole 2-oxide

(+)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)-methyl-2-methylpropyl]-S-methyl-S-(4-methylphenyl)sulfoximide

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