(E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene

Base Information

• Chemical Name: (E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene
• CAS No.: 341544-08-9
• Molecular Formula: C₃₄H₅₉NO₃Si
• Molecular Weight: 557.933

Synonyms:(E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene

Chemical Property of (E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene

Chemical Property:

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Technology Process of (E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene

There total 2 articles about (E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene 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:

Benzyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-but-(E)-ylidene]-amine + acrolein (R,R)-1,2-dicyclohexylethylene acetal (257861-22-6) → (E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene (341544-08-9) + (E)-(4R,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene

Guidance literature:

acrolein (R,R)-1,2-dicyclohexylethylene acetal; With titanium(IV) isopropylate; isopropylmagnesium chloride; In diethyl ether; at -50 - -40 ℃; for 1.5h;

Benzyl-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-but-(E)-ylidene]-amine; In diethyl ether; at -40 - 20 ℃; for 4h; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ja004140k

Reference yield:

(1R,2R)-1,2-dicyclohexyl-1,2-ethanediol (120850-92-2) → (E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene (341544-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / p-toluenesulfonic acid hydrate / CH₂Cl₂ / 2 h / 20 °C

2.1: Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1.5 h / -50 - -40 °C

2.2: diethyl ether / 4 h / -40 - 20 °C

With titanium(IV) isopropylate; isopropylmagnesium chloride; toluene-4-sulfonic acid; In diethyl ether; dichloromethane;

DOI:10.1021/ja004140k

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene (341544-08-9) → Benzyl-[(E)-(S)-1-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-((1R,2R)-1,2-dicyclohexyl-2-hydroxy-ethoxy)-but-3-enyl]-carbamic acid tert-butyl ester

Guidance literature:

With triethylamine; In tetrahydrofuran; at 50 ℃; for 12h;

DOI:10.1021/ja004140k

upstream raw materials:

acrolein (R,R)-1,2-dicyclohexylethylene acetal

(1R,2R)-1,2-dicyclohexyl-1,2-ethanediol

Downstream raw materials:

methyl (3R_.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate

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