bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane

Base Information

• Chemical Name: bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane
• CAS No.: 1613145-01-9
• Molecular Formula: C₄₅H₅₈I₂O₄Si₂
• Molecular Weight: 972.933

Synonyms:bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane

Chemical Property of bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane

Chemical Property:

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Technology Process of bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane

There total 2 articles about bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane 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: 91.0%

bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane (1613144-91-4) → bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane (1613145-01-9)

Guidance literature:

With sodium iodide; In acetone; at 120 ℃; for 2h; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1039/c4cc02702g

Reference yield:

(S)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate (118629-75-7) → bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane (1613145-01-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / pH > 7 / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 24 h / 20 °C / Inert atmosphere

3.1: sodium iodide / acetone / 2 h / 120 °C / Inert atmosphere; Microwave irradiation; Sealed tube

With 1H-imidazole; trifluoroacetic acid; sodium iodide; In dichloromethane; acetone;

DOI:10.1039/c4cc02702g

Reference yield: 74.0%

bis[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methane (1613145-01-9) → (5S,7S,9S,11S)-5,11-diallyl-2,2,14,14-tetramethyl-3,3,13,13-tetraphenyl-4,12-dioxa-3,13-disilapentadecane-7,9-diol (1613145-13-3)

Guidance literature:

With ammonium chloride; zinc; In ethanol; diastereoselective reaction; Inert atmosphere; Sealed tube; Heating;

DOI:10.1039/c4cc02702g

upstream raw materials:

bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane

(S)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate

Downstream raw materials:

(5S,7S,9S,11S)-5,11-diallyl-2,2,14,14-tetramethyl-3,3,13,13-tetraphenyl-4,12-dioxa-3,13-disilapentadecane-7,9-diol

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