(-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Base Information

• Chemical Name: (-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate
• CAS No.: 473758-97-3
• Molecular Formula: C₂₄H₃₀O₆
• Molecular Weight: 414.499
• Mol file: 473758-97-3.mol

Synonyms:(-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Chemical Property of (-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate

There total 6 articles about (-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate 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%

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal (132969-60-9) + C6H5CO2CH(CH3)C(C2H4)OB(C6H11)2 (473758-96-2) → (-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate (473758-97-3)

Guidance literature:

In diethyl ether; at -78 - -20 ℃; for 16h;

DOI:10.1016/S0040-4039(02)01217-0

Reference yield: 73.0%

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal (132969-60-9) + (-)-(R)-3-oxopentan-2-yl benzoate (460997-47-1) → (-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate (473758-97-3)

Guidance literature:

(-)-(R)-3-oxopentan-2-yl benzoate; With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In diethyl ether; at -78 - 0 ℃; for 2h; Inert atmosphere;

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal; In diethyl ether; at -78 - 0 ℃; for 18.5h; Inert atmosphere;

DOI:10.1021/acs.joc.6b03060

Reference yield:

(-)-(R)-3-oxopentan-2-yl benzoate (460997-47-1) → (-)-(2R,4S,5S,6S)-5-hydroxy-7-((4-methoxybenzyl)oxy)-4,6-dimethyl-3-oxoheptan-2-yl benzoate (473758-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Me₂NEt / diethyl ether / 1 h / 0 °C

2: 94 percent / diethyl ether / 16 h / -78 - -20 °C

With N,N-dimethyl-ethanamine; In diethyl ether;

DOI:10.1016/S0040-4039(02)01217-0

upstream raw materials:

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

C₆H₅CO₂CH(CH₃)C(C₂H₄)OB(C₆H₁₁)2

(-)-(R)-3-oxopentan-2-yl benzoate

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

Downstream raw materials:

Isobutyric acid (5E,11Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-2,4,8,10-tetramethyl-7-oxo-3,9-bis-triethylsilanyloxy-dodeca-5,11-dienyl ester

Isobutyric acid (Z)-(1S,2R,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-9-hydroxy-2,4,8,10-tetramethyl-7-oxo-3-triethylsilanyloxy-dodec-11-enyl ester