5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol

Base Information

• Chemical Name: 5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol
• CAS No.: 110426-22-7
• Molecular Formula: C₁₉H₂₂O₃S
• Molecular Weight: 330.448
• Mol file: 110426-22-7.mol

Synonyms:5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol

Chemical Property of 5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol

There total 11 articles about 5-benzyloxy-1-(S_R)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-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: 92.0%

(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one (110426-21-6) → (2S,3E)-5-benzyloxy-1-(4-methylphenylsulfinyl)-3-penten-2-ol (110426-22-7)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 0.583333h;

DOI:10.1021/jo034157w

Reference yield: 91.0%

(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one (110426-21-6) → 5-benzyloxy-1-(SR)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol (110426-22-7)

Guidance literature:

With diisobutylaluminium hydride; zinc(II) chloride; In tetrahydrofuran; toluene; at -78 ℃; for 0.666667h;

DOI:10.1016/S0957-4166(03)00427-0

Reference yield:

sodium phenyl-methanolate (20194-18-7) → 5-benzyloxy-1-(SR)-(4-methylphenylsulfinyl)-(2R,3E)-penten-2-ol (110426-22-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / nBuN⁺I^- / tetrahydrofuran

2: 80 percent / AcOH

3: 80 percent / K₂CO₃

4: 60 percent / LDA / tetrahydrofuran / 0 °C

5: 90 percent / ZnCl₂, DIBAL / tetrahydrofuran / -78 °C

With diisobutylaluminium hydride; potassium carbonate; acetic acid; zinc(II) chloride; lithium diisopropyl amide; nBuN⁺I^-; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)95649-1

upstream raw materials:

(E)-5-Benzyloxy-1-((R)-toluene-4-sulfinyl)-pent-3-en-2-one

ethyl 2E-4-(benzyloxy)-2-butenoate

benzyloxyacetoaldehyde

2-((benzyloxy)methyl)-1,3-dioxolane

Downstream raw materials:

(2R,3R,4S)-1-Benzyloxy-5-((R)-toluene-4-sulfinyl)-pentane-2,3,4-triol

5-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-pentane-2,3-diol

Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate

4-[2-benzyloxy-1-bromo-(1S)-ethyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4R,5R)-1,3-dioxolane