(3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one

Base Information

• Chemical Name: (3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one
• CAS No.: 1352481-39-0
• Molecular Formula: C₃₆H₅₂O₇Si
• Molecular Weight: 624.89

Synonyms:(3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one

Chemical Property of (3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one

Chemical Property:

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Technology Process of (3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one

There total 10 articles about (3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-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:

2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-2-methylpropanal (1352481-36-7) + (4S,5S)-5-(benzyloxy)-4-(4-methoxybenzyloxy)hexan-2-one (1352481-38-9) → (3R,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one + (3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one (1352481-39-0)

Guidance literature:

(4S,5S)-5-(benzyloxy)-4-(4-methoxybenzyloxy)hexan-2-one; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether; at -100 ℃; for 0.55h; Inert atmosphere;

2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-2-methylpropanal; In diethyl ether; at -100 - -78 ℃; for 7h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol202966m

Reference yield:

(5-bromo-2-furan-2-yl)methanol (27230-58-6) → (3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one (1352481-39-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2.1: lithium dicyclohexylamide / toluene / 0.17 h / 0 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / diethyl ether / 1 h / -78 °C / Inert atmosphere

4.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / diethyl ether / 0.55 h / -100 °C / Inert atmosphere

4.2: 7 h / -100 - -78 °C / Inert atmosphere

With 1H-imidazole; dmap; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; lithium dicyclohexylamide; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; toluene; 4.1: Aldol reaction / 4.2: Aldol reaction;

DOI:10.1021/ol202966m

Reference yield:

5-bromo-furan-2-carboxylic acid (585-70-6) → (3S,7S,8S)-8-(benzyloxy)-2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-3-hydroxy-7-(4-methoxybenzyloxy)-2-methylnonan-5-one (1352481-39-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: borane-THF / tetrahydrofuran / 48 h / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.1: lithium dicyclohexylamide / toluene / 0.17 h / 0 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / diethyl ether / 1 h / -78 °C / Inert atmosphere

5.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / diethyl ether / 0.55 h / -100 °C / Inert atmosphere

5.2: 7 h / -100 - -78 °C / Inert atmosphere

With 1H-imidazole; dmap; borane-THF; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; lithium dicyclohexylamide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 5.1: Aldol reaction / 5.2: Aldol reaction;

DOI:10.1021/ol202966m

upstream raw materials:

(5-bromo-2-furan-2-yl)methanol

5-bromo-furan-2-carboxylic acid

methyl 2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-2-methylpropanoate

2-(5-((tert-butyldimethylsilyloxy)methyl)furan-2-yl)-2-methylpropanal

Downstream raw materials:

(4R,6S)-4-((2S,3S)-3-(benzyloxy)-2-(4-methoxybenzyloxy)butyl)-6-(2-(5-((tertbutyldimethylsilyloxy)methyl)furan-2-yl)propan-2-yl)-2,2-diisopropyl-1,3,2-dioxasilinane

5-(2-((4S,6R)-6-((2S,3S)-3-(benzyloxy)-2-hydroxybutyl)-2,2-diisopropyl-1,3,2-dioxasilinan-4-yl)propan-2-yl)furan-2-carbaldehyde

(E)-((2S,3S)-3-(benzyloxy)-1-((4R,6S)-6-(2-(5-formylfuran-2-yl)propan-2-yl)-2,2-diisopropyl-1,3,2-dioxasilinan-4-yl)butan-2-yl) but-2-enoate

C₃₂H₄₆O₇Si

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