(S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate

Base Information

• Chemical Name: (S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate
• CAS No.: 1554321-47-9
• Molecular Formula: C₃₅H₅₂O₆
• Molecular Weight: 568.794
• Mol file: 1554321-47-9.mol

Synonyms:(S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate

Chemical Property of (S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate

There total 12 articles about (S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate 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: 99.0%

(4S,5S,7R,11R)-5,7-dihydroxy-11-(4-methoxybenzyloxy)-4,6,6-trimethylhexadeca-2,8-diynyl pivalate (1554321-45-7) + 2,2-dimethoxy-propane (77-76-9) → (S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate (1554321-47-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 13.5h; Inert atmosphere;

DOI:10.1021/ol500050p

Reference yield:

(R)-2-hydroxyheptyl p-toluenesulfonate (80800-66-4,120925-79-3) → (S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate (1554321-47-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydride / diethyl ether; mineral oil / 43 h / 0 - 20 °C / Inert atmosphere

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 151 h / 0 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / 143 h / 20 °C / Inert atmosphere

4.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / tetrahydrofuran / 0.35 h / 20 °C / Inert atmosphere

4.2: 48 h / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -30 °C

6.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C / Inert atmosphere

7.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / 74 h / 20 °C

8.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

8.2: 37 h / -78 - -20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5.17 h / 0 - 20 °C

10.1: toluene-4-sulfonic acid / acetone / 13.5 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; palladium diacetate; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone; toluene; mineral oil;

DOI:10.1021/ol500050p

Reference yield:

1-Heptene (592-76-7) → (S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-ynyl pivalate (1554321-47-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: AD-mix-β / tert-butyl alcohol; water / 120 h / 0 °C

2.1: pyridine; dmap / dichloromethane / 171 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydride / diethyl ether; mineral oil / 43 h / 0 - 20 °C / Inert atmosphere

4.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 151 h / 0 - 20 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / dichloromethane / 143 h / 20 °C / Inert atmosphere

6.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / tetrahydrofuran / 0.35 h / 20 °C / Inert atmosphere

6.2: 48 h / 20 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -30 °C

8.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C / Inert atmosphere

9.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / 74 h / 20 °C

10.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

10.2: 37 h / -78 - -20 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5.17 h / 0 - 20 °C

12.1: toluene-4-sulfonic acid / acetone / 13.5 h / 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; AD-mix-β; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; palladium diacetate; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; toluene; mineral oil; tert-butyl alcohol; 1.1: |Sharpless Dihydroxylation;

DOI:10.1021/ol500050p

upstream raw materials:

(R)-2-hydroxyheptyl p-toluenesulfonate

(R)-1,2-epoxyheptane

(R)-(+)-non-1-yn-4-ol

1-Heptene

Downstream raw materials:

(S)-4-((4S,6R)-6-((R)-4-(4-methoxybenzyloxy)non-1-ynyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-yn-1-ol

(S,Z)-4-((4S,6S)-6-((R,Z)-4-(4-methoxybenzyloxy)-1-(triphenylstannyl)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-(triphenylstannyl)pent-2-en-1-ol

C₇₂H₉₀O₅SiSn₂

tert-butyl((S,Z)-2-iodo-4-((4S,6S)-6-((R,Z)-1-iodo-4-(4-methoxybenzyloxy)non-1-enyl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)pent-2-enyloxy)dimethylsilane