(2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one

Base Information

• Chemical Name: (2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one
• CAS No.: 199857-44-8
• Molecular Formula: C₂₅H₄₄O₅Si
• Molecular Weight: 452.707
• Mol file: 199857-44-8.mol

Synonyms:(2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one

Chemical Property of (2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one

There total 8 articles about (2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one 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: 97.0%

3-(p-methoxybenzyloxy)propanal (128461-65-4) + C34H63BO2Si (199857-43-7) → (2S,5R)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one + (2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one (199857-44-8)

Guidance literature:

- 78 deg C, 5-6 h then -20 deg C, 16 h;

DOI:10.1016/S0040-4039(97)10126-5

Reference yield:

3-(p-methoxybenzyloxy)propanal (128461-65-4) + C34H63BO2Si (199857-43-7) → (2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one (199857-44-8)

Guidance literature:

3-(p-methoxybenzyloxy)propanal; C₃₄H₆₃BO₂Si; In diethyl ether; at -78 - -20 ℃; for 21h;

With dihydrogen peroxide; In methanol; at 20 ℃; for 2.5h;

DOI:10.1039/b504146e

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (2S,5S)-5-hydroxy-7-(p-methoxybenzyloxy)-2-methyl-1-(triisopropylsiloxy)-heptan-3-one (199857-44-8)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; dmap; isopropylmagnesium chloride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/b504146e

upstream raw materials:

3-(p-methoxybenzyloxy)propanal

C₃₄H₆₃BO₂Si

C₃₄H₆₃BO₂Si

triisopropylsilyl chloride

Downstream raw materials:

(2S,5S)-7-(4-Methoxy-benzyloxy)-2-methyl-5-triethylsilanyloxy-1-triisopropylsilanyloxy-heptan-3-one

Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-10-methyl-8-((R)-3-methyl-2-methylene-4-triisopropylsilanyloxy-butyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

Acetic acid (2S,4S,6R,8S,10S)-2-(2-benzyloxy-ethyl)-10-hydroxy-8-((R)-4-hydroxy-3-methyl-2-methylene-butyl)-10-methyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

(4S,5S,6R,9S)-5-Hydroxy-9-methoxy-11-(4-methoxy-benzyloxy)-2,4,6-trimethyl-7-methylene-undecan-3-one