(S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one

Base Information

• Chemical Name: (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one
• CAS No.: 1371603-83-6
• Molecular Formula: C₃₃H₄₆O₅Si
• Molecular Weight: 550.811

Synonyms:(S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one

Chemical Property of (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one

There total 11 articles about (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-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: 95.0%

(S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one (1371603-82-5) → (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one (1371603-83-6)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jo3004106

Reference yield:

(5S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-heptyl)-5-methyl-3-(phenylthio)dihydrofuran-2(3H)-one → (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one (1371603-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 0.5 h / Reflux; Inert atmosphere

2.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere

With pyridine; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo3004106

Reference yield:

1-(4-Methoxybenzyloxy)pent-4-yn-2-ol (214914-86-0) → (S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one (1371603-83-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.5 h / 20 °C / Inert atmosphere

2.2: 2 h / Inert atmosphere

3.1: 5%-palladium/activated carbon; hydrogen / ethanol / 60 h / 20 °C / 760.05 Torr / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.75 h / 0 - 20 °C / pH 7 / aq. phosphate buffer; Inert atmosphere

5.1: pyridine / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

5.2: 0.67 h / -78 - -30 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / -78 - 0 °C / Inert atmosphere

6.2: 0.5 h / 0 °C / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.2: 0.5 h / Reflux; Inert atmosphere

8.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 5%-palladium/activated carbon; hydrogen; pyridine hydrogenfluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo3004106

upstream raw materials:

(R)-tert-butyl((1-((4-methoxybenzyl)oxy)pent-4-yn-2-yl)-oxy)diphenylsilane

tert-butyl(((2S,5S)-5-((R,Z)-6-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl) oxy)hept-1-en-3-yn-1-yl)tetrahydrofuran-2-yl)methoxy)diphenylsilane

(S)-3-((R)-2-((tert-butyldiphenylsilyl)oxy)-7-((2R,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2-yl)heptyl)-5-methylfuran-2(5H)-one

(2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxaldehyde

Downstream raw materials:

C₃₃H₄₄O₅Si

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