tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane

Base Information

• Chemical Name: tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane
• CAS No.: 1185750-51-9
• Molecular Formula: C₃₆H₄₈O₄Si₂
• Molecular Weight: 600.946

Synonyms:tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane

Chemical Property of tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane

Chemical Property:

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Technology Process of tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane

There total 7 articles about tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane 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: 93.0%

(3S,4S,5S,6S)-7-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-4,6-dimethyl-1-(trimethylsilyl)hept-1-yn-3-ol (1185750-24-6) → tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane (1185750-51-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tet.2009.04.073

Reference yield:

(2S,3R,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylhex-5-en-1-ol (1044739-29-8) → tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane (1185750-51-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; triethylamine / dichloromethane / Inert atmosphere

2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone / 48 h / 20 °C / pH 7 / aq. buffer; Inert atmosphere

3.1: sodium periodate / tetrahydrofuran / 2 h / 0 - 20 °C / pH 7 / aq. buffer

4.1: diethylzinc / toluene / 1 h / Inert atmosphere; Reflux

4.2: 1 h / 20 °C / Inert atmosphere

4.3: Inert atmosphere

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C / Molecular sieve; Inert atmosphere

With dmap; sodium periodate; osmium(VIII) oxide; diethylzinc; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetone; toluene;

DOI:10.1016/j.tet.2009.04.073

Reference yield:

(2R,4R,5S)-4-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (1185750-49-5) → tert-butyl((S)-2-((2S,4S,5R,6S)-2-(4-methoxyphenyl)-5-methyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)propoxy)diphenylsilane (1185750-51-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / hexane; toluene / 3.5 h / -78 - 0 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / Inert atmosphere

3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone / 48 h / 20 °C / pH 7 / aq. buffer; Inert atmosphere

4.1: sodium periodate / tetrahydrofuran / 2 h / 0 - 20 °C / pH 7 / aq. buffer

5.1: diethylzinc / toluene / 1 h / Inert atmosphere; Reflux

5.2: 1 h / 20 °C / Inert atmosphere

5.3: Inert atmosphere

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C / Molecular sieve; Inert atmosphere

With dmap; sodium periodate; osmium(VIII) oxide; diethylzinc; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene;

DOI:10.1016/j.tet.2009.04.073

upstream raw materials:

(2S,3R,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylhex-5-en-1-ol

(3S,4S,5S,6S)-7-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-4,6-dimethyl-1-(trimethylsilyl)hept-1-yn-3-ol

(2R,4R,5S)-4-((S)-but-3-en-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

(3S,4R,5S)-4-(4-methoxybenzyloxy)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhex-1-ene

Downstream raw materials:

(2S,4S,5R,6S)-4-ethynyl-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

(S)-2-((2S,4S,5R,6S)-6-ethynyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)propan-1-ol

(2S,3R,4S,5E,7E)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S,Z)-hexa-3,5-dien-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethylocta-5,7-dien-3-ol

(2S,3R,4S,6S)-1-(benzyloxy)-8-((2R,4R,5S,6S)-6-((S)-hexan-2-yl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)-2,4,6-trimethyloctan-3-ol

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