(5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol

Base Information

• Chemical Name: (5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol
• CAS No.: 1613145-15-5
• Molecular Formula: C₃₁H₄₆O₅Si
• Molecular Weight: 526.789

Synonyms:(5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol

Chemical Property of (5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol

Chemical Property:

Purity/Quality:

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Technology Process of (5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol

There total 2 articles about (5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol 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: 84.0%

tert-butyl{(2S,4R,6S)-2-(iodomethyl)-6-[((2R,4S,6R)-6-(iodomethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-4-yloxy}diphenylsilane (1613145-03-1) → (5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol (1613145-15-5)

Guidance literature:

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

DOI:10.1039/c4cc02702g

Reference yield:

(2S,4S,6R)-2-{[(2S,4R,6S)-4-(tert-butyldiphenylsilyl)oxy-6-(iodomethyl)tetrahydro-2H-pyran-2-yl]methyl}-6-(iodomethyl)tetrahydro-2H-pyran-4-ol (1613144-95-8) → (5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol (1613145-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere

2: zinc; ammonium chloride / ethanol / Inert atmosphere; Sealed tube; Heating

With ammonium chloride; N-ethyl-N,N-diisopropylamine; zinc; In ethanol; dichloromethane;

DOI:10.1039/c4cc02702g

Reference yield: 88.0%

(5R,7R,9S,11S)-5,11-diallyl-14,14-dimethyl-13,13-diphenyl-2,4,12-trioxa-13-silapentadecane-7,9-diol (1613145-15-5) + 2,2-dimethoxy-propane (77-76-9) → tert-butyl{(S)-1-[(4S,6S)-6-((R)-2-(methoxymethoxy)pent-4-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl]pent-4-en-2-yloxy}diphenylsilane (1613145-18-8)

Guidance literature:

With pyridinium p-toluenesulfonate; In acetone; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1039/c4cc02702g

upstream raw materials:

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

tert-butyl{(2S,4R,6S)-2-(iodomethyl)-6-[((2R,4S,6R)-6-(iodomethyl)-4-(methoxymethoxy)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-4-yloxy}diphenylsilane

Downstream raw materials:

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

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