(4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS No.: 1403608-18-3
• Molecular Formula: C₃₈H₅₀O₅Si
• Molecular Weight: 614.897
• Mol file: 1403608-18-3.mol

Synonyms:(4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane

There total 22 articles about (4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane 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: 75.0%

(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1403608-11-6) + 5-{[(3R)-3-{[tert-butyl(diphenyl)silyl]oxy}butyl]sulfonyl}-1-phenyl-1H-tetrazole (1403608-12-7) → (4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane (1403608-18-3)

Guidance literature:

5-{[(3R)-3-{[tert-butyl(diphenyl)silyl]oxy}butyl]sulfonyl}-1-phenyl-1H-tetrazole; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; for 0.5h; Cooling;

(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde; In tetrahydrofuran; toluene; at 20 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Cooling;

DOI:10.1002/ejoc.201200241

Reference yield:

(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (1403608-11-6) + 5-{[(3R)-3-{[tert-butyl(diphenyl)silyl]oxy}butyl]sulfonyl}-1-phenyl-1H-tetrazole (1403608-12-7) → (4S,5S)-4-[(R,Z)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane + (4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane (1403608-18-3)

Guidance literature:

5-{[(3R)-3-{[tert-butyl(diphenyl)silyl]oxy}butyl]sulfonyl}-1-phenyl-1H-tetrazole; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; for 0.5h; Cooling;

(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde; In tetrahydrofuran; toluene; at 20 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Cooling;

DOI:10.1002/ejoc.201200241

Reference yield:

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (866022-02-8) → (4S,5S)-4-[(R,E)-4-tert-butyldiphenylsilyloxypent-1-enyl]-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane (1403608-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

1.2: 2 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h

4.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / Cooling

4.2: 2 h / 20 °C / Cooling

With 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 4.1: Julia-Kocienski olefination / 4.2: Julia-Kocienski olefination;

DOI:10.1002/ejoc.201200241

upstream raw materials:

(S)-1-((4S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

tert-butyl-[(R)-3-(4-methoxy-benzyloxy)-1-methylpropoxy]-diphenyl-silane

(4R,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

5-{[(3R)-3-{[tert-butyl(diphenyl)silyl]oxy}butyl]sulfonyl}-1-phenyl-1H-tetrazole

Downstream raw materials:

(R,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-ol

(S,E)-5-{(4S,5S)-5-[(S)-1-(4-methoxybenzyloxy)but-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

(R,E)-5-{(4S,5S)-5-[(S)-1-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl}pent-4-en-2-yl 2-hydroxy-4-methoxy-6-vinylbenzoate

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