(4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene

Base Information

• Chemical Name: (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene
• CAS No.: 862379-31-5
• Molecular Formula: C₃₃H₄₉NO₇Si
• Molecular Weight: 599.84

Synonyms:(4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene

Chemical Property of (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene

There total 11 articles about (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-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: 94.0%

(4R)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(triethylsiloxy)-hex-1-ene (199857-46-0) + 4-nitro-benzoic acid (62-23-7) → (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene (862379-31-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; at 20 ℃; for 0.333333h;

DOI:10.1039/b504146e

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene (862379-31-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 99 percent / imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

2.1: 99.5 g / i-PrMgCl / tetrahydrofuran / 1 h / -20 °C

3.1: 75 percent / tetrahydrofuran; diethyl ether / 3 h / 0 °C

4.1: Et₃N / diethyl ether / -78 - 0 °C

5.1: diethyl ether / 21 h / -78 - -20 °C

5.2: 4.08 g / aq. H₂O₂ / methanol / 2.5 h / 20 °C

6.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

7.1: Zn; PbI₂; TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 4.5 h / 20 °C

8.1: 5.64 g / PPTS / methanol; CH₂Cl₂ / 0.5 h / 20 °C

9.1: 94 percent / Ph₃P; DEAD / benzene / 0.33 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; triphenylphosphine; lead(II) iodide; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene; 9.1: Mitsunobu inversion;

DOI:10.1039/b504146e

Reference yield:

(S)-methyl 2-methyl-3-(triisopropylsilyloxy)propanoate (158783-84-7) → (4S)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(p-nitrobenzoyloxy)-hex-1-ene (862379-31-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 99.5 g / i-PrMgCl / tetrahydrofuran / 1 h / -20 °C

2.1: 75 percent / tetrahydrofuran; diethyl ether / 3 h / 0 °C

3.1: Et₃N / diethyl ether / -78 - 0 °C

4.1: diethyl ether / 21 h / -78 - -20 °C

4.2: 4.08 g / aq. H₂O₂ / methanol / 2.5 h / 20 °C

5.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

6.1: Zn; PbI₂; TiCl₄ / tetrahydrofuran; CH₂Cl₂ / 4.5 h / 20 °C

7.1: 5.64 g / PPTS / methanol; CH₂Cl₂ / 0.5 h / 20 °C

8.1: 94 percent / Ph₃P; DEAD / benzene / 0.33 h / 20 °C

With 2,6-dimethylpyridine; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; triphenylphosphine; lead(II) iodide; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene; 8.1: Mitsunobu inversion;

DOI:10.1039/b504146e

upstream raw materials:

(4R)-2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-6-(p-methoxybenzyloxy)-4-(triethylsiloxy)-hex-1-ene

4-nitro-benzoic acid

triisopropylsilyl chloride

(S)-methyl 2-methyl-3-(triisopropylsilyloxy)propanoate

Downstream raw materials:

(2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol

(2S,4S,6R,8S,10S)-8-(2-benzyloxyethyl)-10-(t-butyldimethylsiloxy)-4-methyl-2-{2-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-allyl}-1,7-dioxaspiro[5.5]undecan-4-ol

(2S,6R,8S,10S)-8-(2-Benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-2-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undecan-4-one

(3S,5S,9S,11S)-1-benzyloxy-5-(t-butyldimethylsiloxy)-9-hydroxy-13-[1-(triisopropylsiloxy)-prop-2-(R)-yl]-3,11-bis(triethylsiloxy)-tetradec-13-en-7-one

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