2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane

Base Information

• Chemical Name: 2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane
• CAS No.: 82130-82-3
• Molecular Formula: C₂₃H₂₉ClO₄S
• Molecular Weight: 437
• Mol file: 82130-82-3.mol

Synonyms:2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane

Chemical Property of 2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane

There total 9 articles about 2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane 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: 72.0%

lithio α-chloromethyl phenyl sulfoxide (41103-65-5) + 2-((S)-2-Benzyloxy-3-iodo-propyl)-5,5-dimethyl-[1,3]dioxane (82130-81-2) → 2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane (82130-82-3)

Guidance literature:

DOI:10.1016/S0040-4039(00)86913-0

Reference yield:

(S)-4-benzyloxy-dihydrofuran-2(3H)-one (101999-38-6,114784-20-2,121961-93-1,82130-75-4) → 2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane (82130-82-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / diisobutyl aluminium hydride / -40 °C

2: p-toluene sulphonic acid

3: acidic conditions

5: NaI / acetone

6: 72 percent

With diisobutylaluminium hydride; sodium iodide; toluene-4-sulfonic acid; In acetone;

DOI:10.1016/S0040-4039(00)86913-0

Reference yield:

benzyl bromide (100-39-0) → 2-((S)-4-Benzenesulfinyl-2-benzyloxy-4-chloro-butyl)-5,5-dimethyl-[1,3]dioxane (82130-82-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / Ag₂O / ethyl acetate / Ambient temperature

2: 1) saponification of the ester functions, 2) acetyl chloride, reflux

3: NaBH₄ / tetrahydrofuran

4: 65 percent / diisobutyl aluminium hydride / -40 °C

5: p-toluene sulphonic acid

6: acidic conditions

8: NaI / acetone

9: 72 percent

With sodium tetrahydroborate; diisobutylaluminium hydride; sodium iodide; silver(l) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; ethyl acetate; acetone;

DOI:10.1016/S0040-4039(00)86913-0

upstream raw materials:

lithio α-chloromethyl phenyl sulfoxide

2-((S)-2-Benzyloxy-3-iodo-propyl)-5,5-dimethyl-[1,3]dioxane

(S)-4-benzyloxy-dihydrofuran-2(3H)-one

benzyl bromide

Downstream raw materials:

2-((S)-2-Benzyloxy-but-3-ynyl)-5,5-dimethyl-[1,3]dioxane

2-((E)-(S)-2-Benzyloxy-4-chloro-but-3-enyl)-5,5-dimethyl-[1,3]dioxane