(S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane

Base Information

• Chemical Name: (S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane
• CAS No.: 275825-09-7
• Molecular Formula: C₁₉H₂₈O₅S
• Molecular Weight: 368.494
• Mol file: 275825-09-7.mol

Synonyms:(S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane

Chemical Property of (S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane

There total 4 articles about (S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane 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: 97.0%

p-toluenesulfonyl chloride (98-59-9) + (S)-2-methyl-2-(3-hydroxypropyl)cyclohexanone ethylene ketal (171737-76-1) → (S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane (275825-09-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/anie.201510708

Reference yield:

(S)-3-(1-methyl-2-oxocyclohexyl)-propionic acid methyl ester (53068-89-6,94089-47-1,150927-14-3,112898-44-9) → (S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane (275825-09-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / benzene / Heating

2: 90 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3: 92 percent / pyridine / 0 °C

With lithium aluminium tetrahydride; In tetrahydrofuran; pyridine; benzene; 1: cyclocondensation / 2: Reduction / 3: Tosylation;

DOI:10.1016/S0040-4039(00)00078-2

Reference yield:

3-((S)-6-Methyl-1,4-dioxa-spiro[4.5]dec-6-yl)-propionic acid methyl ester (275825-11-1) → (S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane (275825-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / LiAlH₄ / tetrahydrofuran / 0 °C

2: 92 percent / pyridine / 0 °C

With lithium aluminium tetrahydride; In tetrahydrofuran; pyridine; 1: Reduction / 2: Tosylation;

DOI:10.1016/S0040-4039(00)00078-2

upstream raw materials:

p-toluenesulfonyl chloride

(S)-2-methyl-2-(3-hydroxypropyl)cyclohexanone ethylene ketal

(S)-3-(1-methyl-2-oxocyclohexyl)-propionic acid methyl ester

3-((S)-6-Methyl-1,4-dioxa-spiro[4.5]dec-6-yl)-propionic acid methyl ester

Downstream raw materials:

Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester

(S)-6-methyl-6-(4-methylpent-4-en-1-yl)-1-vinylcyclohex-1-ene

(S)-2-methyl-2-(4-methylpent-4-en-1-yl)cyclohexanone