(S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propan-1-ol

Base Information

• Chemical Name: (S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propan-1-ol
• CAS No.: 333335-29-8
• Molecular Formula: C₁₅H₂₂O₅S
• Molecular Weight: 314.403
• Mol file: 333335-29-8.mol

Synonyms:(S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propan-1-ol

Chemical Property of (S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propan-1-ol

There total 6 articles about (S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-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:

Benzoic acid (S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propyl ester → (S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propan-1-ol (333335-29-8)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -70 ℃;

DOI:10.1055/s-2001-9717

Reference yield:

3-((4-methylphenyl)sulfonyl)propanal (63305-65-7) → (S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propan-1-ol (333335-29-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / NaH / tetrahydrofuran / 0 °C

2: 90 percent / DIBALH / diethyl ether / -70 °C

3: 84 percent / Ti(Oi-Pr)4; (-)-DIPT; t-BuOOH / 3 Angstroem molecular sieves / CH₂Cl₂

4: 73 percent / Ti(Oi-Pr)4 / CH₂Cl₂

5: p-TsOH / dimethylsulfoxide

6: DIBALH / diethyl ether / -70 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; 3 A molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; 1: Wittig-Horner reaction / 3: Sharpless asymmetric epoxidation;

DOI:10.1055/s-2001-9717

Reference yield:

(E)-5-(Toluene-4-sulfonyl)-pent-2-en-1-ol (333335-37-8) → (S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propan-1-ol (333335-29-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / Ti(Oi-Pr)4; (-)-DIPT; t-BuOOH / 3 Angstroem molecular sieves / CH₂Cl₂

2: 73 percent / Ti(Oi-Pr)4 / CH₂Cl₂

3: p-TsOH / dimethylsulfoxide

4: DIBALH / diethyl ether / -70 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; 3 A molecular sieve; In diethyl ether; dichloromethane; dimethyl sulfoxide; 1: Sharpless asymmetric epoxidation;

DOI:10.1055/s-2001-9717

upstream raw materials:

3-((4-methylphenyl)sulfonyl)propanal

(E)-5-(Toluene-4-sulfonyl)-pent-2-en-1-ol

{(2R,3R)-3-[2-(Toluene-4-sulfonyl)-ethyl]-oxiranyl}-methanol

(E)-5-(Toluene-4-sulfonyl)-pent-2-enoic acid ethyl ester

Downstream raw materials:

tert-Butyl-[(S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-(toluene-4-sulfonyl)-propoxy]-diphenyl-silane

(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(toluene-4-sulfonyl)-pentane-1,2-diol

1-[(E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-hepta-4,6-diene-1-sulfonyl]-4-methyl-benzene

4-(tert-butyl-dimethyl-silanyloxy)-6-[1-(tert-butyl-diphenyl-silanyloxy)-3-(toluene-4-sulfonyl)-propyl]-2-(dimethyl-[1,3]dioxolan-4-yl)-3,6-dihydro-2H-pyran