(1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4⁽⁵⁾-ene

Base Information

• Chemical Name: (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4⁽⁵⁾-ene
• CAS No.: 1352125-86-0
• Molecular Formula: C₃₂H₄₂O₅Si
• Molecular Weight: 534.768

Synonyms:(1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4⁽⁵⁾-ene

Chemical Property of (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4⁽⁵⁾-ene

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4⁽⁵⁾-ene

There total 17 articles about (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4⁽⁵⁾-ene 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: 52.0%

(1S,5R,6S)-1,5-dimethyl-5(6)-epoxy-4,9-dioxo-8-oxabicyclo[4.3.0]nonane (1352125-84-8) + (R)-(E)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenyltrifluoromethane sulfonate → (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4(5)-ene (1352125-86-0)

Guidance literature:

(1S,5R,6S)-1,5-dimethyl-5⁽⁶⁾-epoxy-4,9-dioxo-8-oxabicyclo[4.3.0]nonane; With trimesitylborane; sodium; In tetrahydrofuran; at -78 ℃; for 24h; Inert atmosphere;

(R)-(E)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenyltrifluoromethane sulfonate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; at -78 ℃; for 0.75h; Inert atmosphere;

With water; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; at -78 - 20 ℃; pH=7.5; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.067

Reference yield:

(R)-(E)-(+)-ethyl-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenoate (917871-10-4) → (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4(5)-ene (1352125-86-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / diethyl ether; hexane / 5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; hexane / 0.17 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: trimesitylborane; sodium / tetrahydrofuran / 24 h / -78 °C / Inert atmosphere

3.2: 0.75 h / -78 °C / Inert atmosphere

3.3: -78 - 20 °C / pH 7.5 / Inert atmosphere

With trimesitylborane; tert.-butyl lithium; sodium; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1016/j.tet.2011.09.067

Reference yield:

(1R,4S)-2-((3R,4S)-2,4-dimethyl-3-triisopropylsiloxymethylcyclohex-2-en-1-one-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one (1352125-79-1) → (1S,6S)-(+)-4-[(4R,E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenyloxy]-1,5-dimethyl-6-hydroxy-9-oxo-8-oxabicyclo[4.3.0]non-4(5)-ene (1352125-86-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere

2.1: sodium tetrahydroborate / ethanol / 20 h / 0 - 20 °C / Inert atmosphere

3.1: sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 10 h / 0 °C / Inert atmosphere

4.1: dipyridinium dichromate / dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

5.1: trimesitylborane; sodium / tetrahydrofuran / 24 h / -78 °C / Inert atmosphere

5.2: 0.75 h / -78 °C / Inert atmosphere

5.3: -78 - 20 °C / pH 7.5 / Inert atmosphere

With sodium tetrahydroborate; sodium dihydrogenphosphate; dipyridinium dichromate; trimesitylborane; tetrabutyl ammonium fluoride; sodium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.tet.2011.09.067

upstream raw materials:

(R)-(E)-(+)-ethyl-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenoate

(1R,4S)-2-((3R,4S)-2,4-dimethyl-3-triisopropylsiloxymethylcyclohex-2-en-1-one-4-carbonyl)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

C₁₀H₁₄O₃

C₁₀H₁₄O₄

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