(7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

Base Information

Chemical Name:(7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate
CAS No.:1460293-50-8
Molecular Formula:C₃₉H₇₀O₉Si
Molecular Weight:711.065
Hs Code.:

(7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

Synonyms:(7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

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Chemical Property of (7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

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Technology Process of (7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

There total 11 articles about (7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl 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:

: 1460293-49-5
(S,E)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)undec-7-en-1-yl pivalate

: 1460293-50-8
(7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

: (10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

Guidance literature:: With methanesulfonamide; In water; tert-butyl alcohol; at 20 ℃; Overall yield = 77%; Overall yield = 12.0 mg; diastereoselective reaction;
DOI:10.1039/c3ob41569d

Reference yield:

: 1460293-45-1
(4S)-4-((1,3-dithian-2-yl)methyl)-2-(4-methoxyphenyl)-1,3-dioxane

: 1460293-50-8
(7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

: (10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

Guidance literature:: Multi-step reaction with 7 steps

1.1: diisobutylaluminium hydride / toluene; dichloromethane / 4 h / -78 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - -10 °C

3.2: 2 h / -78 °C

4.1: bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; water / 0.02 h / 20 °C

5.1: zinc(II) tetrahydroborate / diethyl ether / 2 h / -78 °C

6.1: pyridinium p-toluenesulfonate / acetone / 20 °C

7.1: methanesulfonamide / tert-butyl alcohol; water / 20 °C

With 1H-imidazole; n-butyllithium; zinc(II) tetrahydroborate; methanesulfonamide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1039/c3ob41569d

Reference yield:

: (S)-11-hydroxy-10-methylundec-7-enyl pivalate

: 1460293-50-8
(7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

: (10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

1.2: -78 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - -10 °C

2.2: 2 h / -78 °C

3.1: bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran; methanol; water / 0.02 h / 20 °C

4.1: zinc(II) tetrahydroborate / diethyl ether / 2 h / -78 °C

5.1: pyridinium p-toluenesulfonate / acetone / 20 °C

6.1: methanesulfonamide / tert-butyl alcohol; water / 20 °C

With n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; methanesulfonamide; pyridinium p-toluenesulfonate; dimethyl sulfoxide; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; tert-butyl alcohol; 1.2: |Swern Oxidation;
DOI:10.1039/c3ob41569d