tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate

Base Information

• Chemical Name: tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate
• CAS No.: 1613145-16-6
• Molecular Formula: C₃₄H₅₀O₆Si
• Molecular Weight: 582.853

Synonyms:tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate

Chemical Property of tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate

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Technology Process of tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate

There total 2 articles about tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate 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: 87.0%

tert-butyl {(2R,4S,6R)-2-[((2S,4S,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2Hpyran-2-yl)methyl]-6-(iodomethyl)tetrahydro-2H-pyran-4-yl} carbonate (1613145-04-2) → tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate (1613145-16-6)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; at 70 ℃; for 1h; diastereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1039/c4cc02702g

Reference yield:

(2S,4S,6R)-2-{[(2S,4S,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methyl}-6-(iodomethyl)tetrahydro-2H-pyran-4-ol (1613144-99-2) → tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate (1613145-16-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; dmap / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere

2: zinc; ammonium chloride / tetrahydrofuran; water / 1 h / 70 °C / Inert atmosphere; Sealed tube

With dmap; ammonium chloride; triethylamine; zinc; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c4cc02702g

Reference yield: 88.0%

tert-butyl [(4R,6R,8S,10R)-10-(tert-butyldiphenylsilyl)oxy-6,8-dihydroxytrideca-1,12-dien-4-yl]carbonate (1613145-16-6) + 2,2-dimethoxy-propane (77-76-9) → tert-butyl {(R)-1-[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]pent-4-en-2-yl} carbonate (1613145-19-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In acetone; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c4cc02702g

upstream raw materials:

(2S,4S,6R)-2-{[(2S,4S,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methyl}-6-(iodomethyl)tetrahydro-2H-pyran-4-ol

tert-butyl {(2R,4S,6R)-2-[((2S,4S,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2Hpyran-2-yl)methyl]-6-(iodomethyl)tetrahydro-2H-pyran-4-yl} carbonate

Downstream raw materials:

(4S,6S)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

(4S,6R)-4-{[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl}-6-(iodomethyl)-1,3-dioxan-2-one

tert-butyl {(R)-1-[(4R,6S)-6-((R)-2-(tert-butyldiphenylsilyloxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]pent-4-en-2-yl} carbonate

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