(Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one

Base Information

• Chemical Name: (Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one
• CAS No.: 218168-21-9
• Molecular Formula: C₁₉H₂₀O₄S
• Molecular Weight: 344.431
• Mol file: 218168-21-9.mol

Synonyms:(Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one

Chemical Property of (Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one

There total 2 articles about (Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one 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:

benzyl bromide (100-39-0) → (Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one (218168-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / Ambient temperature

2: 1.) LDA / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 30 min

With tetra-(n-butyl)ammonium iodide; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0957-4166(98)00301-2

Reference yield:

ethyl benzyloxyacetate (32122-09-1) + 1-((S)-Toluene-4-sulfinyl)-propan-2-one (127583-42-0) → (Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one (218168-21-9)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 30 min;

DOI:10.1016/S0957-4166(98)00301-2

Reference yield: 51.0%

(Z)-5-Benzyloxy-4-hydroxy-1-((S)-toluene-4-sulfinyl)-pent-3-en-2-one (218168-21-9) → (R)-1-Benzyloxy-4-hydroxy-5-((S)-toluene-4-sulfinyl)-pentan-2-one (218168-24-2)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;

DOI:10.1016/S0957-4166(98)00301-2

upstream raw materials:

ethyl benzyloxyacetate

1-((S)-Toluene-4-sulfinyl)-propan-2-one

benzyl bromide

Downstream raw materials:

(R)-1-Benzyloxy-4-hydroxy-5-((S)-toluene-4-sulfinyl)-pentan-2-one

(+)-[(4R,6R)-6-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]methanol

(R)-1-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-2-ol

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