2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol

Base Information

• Chemical Name: 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol
• CAS No.: 1344673-81-9
• Molecular Formula: C₅₉H₈₄O₅Si₃
• Molecular Weight: 957.569

Synonyms:

Chemical Property of 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol

There total 24 articles about 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol 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:

methyl 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}acrylate → 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol (1344673-81-9)

Guidance literature:

With diisobutylaluminium hydride; In hexane; at -78 ℃; Inert atmosphere;

DOI:10.1002/anie.201104447

Reference yield:

2-[(2R,4S,5S,6R,7R)-7-[((1S,2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentyl)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate (1344673-78-4) → 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol (1344673-81-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere

6.1: diethyl ether / 0 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

8.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

9.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

9.2: -78 °C / Inert atmosphere

10.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / methanol; toluene / 50 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; potassium tert-butylate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction / 3.2: Wittig reaction;

DOI:10.1002/anie.201104447

Reference yield:

[(2R,4S,5S,6R,7R)-7-[((1S,2R,4S,5S)-5-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxy-2-hydroxy-2-methylcyclopentyl)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]acetaldehyde (1344673-93-3) → 2-{(1S,2S,3R,5S)-2-{[(2R,4S,5S,6R,7R)-6-allyl-2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-5-{[tert-butyl(diphenyl)silyl]oxy}-3-methyl-3-[(trimethylsilyl)oxy]cyclopentyl}prop-2-en-1-ol (1344673-81-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / ethanol / 20 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C / Inert atmosphere

4.1: diethyl ether / 0 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

6.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

7.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

7.2: -78 °C / Inert atmosphere

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / methanol; toluene / 50 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: Wittig reaction / 1.2: Wittig reaction;

DOI:10.1002/anie.201104447

upstream raw materials:

(-)-tert-butyl-[(2R,4S,5S,6R,7S)-7-methoxymethoxymethyl-4,7-dimethyl-6-vinyl-1-oxaspiro[4.4]non-2-ylmethoxy]diphenylsilane

2-[(2R,4S,5S,6R,7S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-7-[(methoxymethoxy)methyl]-4,7-dimethyl-1-oxaspiro[4.4]nonan-6-yl]ethan-1-ol

(2R,3S,4S)-2-bromo-3-(tert-butyldimethylsilyl)oxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

(2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

Downstream raw materials:

(1R,2S,3S,4S)-4-(benzyloxy)-2-{[(2R,4S,5S,6R,7R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4,7-dimethyl-6-prop-2-en-1-yl-1-oxaspiro[4.4]non-7-yl]methyl}-3-[1-(hydroxymethyl)ethenyl]-1-methylcyclopentanol

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