(3S)-3-<(1'R)-1'-hydroxy-3'-methylbutyl>-8-methoxy-3,4-dihydroisocoumarin

Base Information

• Chemical Name: (3S)-3-<(1'R)-1'-hydroxy-3'-methylbutyl>-8-methoxy-3,4-dihydroisocoumarin
• CAS No.: 143427-07-0
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 143427-07-0.mol

Synonyms:

Chemical Property of (3S)-3-<(1'R)-1'-hydroxy-3'-methylbutyl>-8-methoxy-3,4-dihydroisocoumarin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-<(1'R)-1'-hydroxy-3'-methylbutyl>-8-methoxy-3,4-dihydroisocoumarin

There total 1 articles about (3S)-3-<(1'R)-1'-hydroxy-3'-methylbutyl>-8-methoxy-3,4-dihydroisocoumarin 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:

carbon dioxide (124-38-9,18923-20-1) + (2S,3R)-1-(3-Methoxy-phenyl)-5-methyl-hexane-2,3-diol (143427-06-9) → 4-((2S,3R)-2,3-Dihydroxy-5-methyl-hexyl)-2-methoxy-benzoic acid (143427-09-2) + (3S)-3-<(1'R)-1'-hydroxy-3'-methylbutyl>-8-methoxy-3,4-dihydroisocoumarin (143427-07-0)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Yield given. Multistep reaction. Yields of byproduct given; 1.) hexane, reflux, 6 h, 2.) hexane,;

DOI:10.1246/cl.1992.1255

Reference yield:

(3S)-3-<(1'R)-1'-hydroxy-3'-methylbutyl>-8-methoxy-3,4-dihydroisocoumarin (143427-07-0) → 2-(benzyloxy)-N-((S)-1-((S)-8-methoxy-1-oxoisochroman-3-yl)-3-methylbutyl)acetamide

Guidance literature:

Multi-step reaction with 3 steps

1: diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / 2 h / 20 °C

3: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 8 h / -10 °C / Inert atmosphere

With diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.1c02576

Reference yield:

(3S)-3-<(1'R)-1'-hydroxy-3'-methylbutyl>-8-methoxy-3,4-dihydroisocoumarin (143427-07-0) → Y-05460M-A (126262-07-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / 2 h / 20 °C

3.1: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / Inert atmosphere

3.2: -78 - -60 °C / Inert atmosphere

With diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.1c02576

upstream raw materials:

carbon dioxide

(2S,3R)-1-(3-Methoxy-phenyl)-5-methyl-hexane-2,3-diol

Downstream raw materials:

6-<<1(S)-<3(S),4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl>-3-methylbutyl>amino>-4(S),5(S)-dihydroxy-6-oxo-3(S)-ammoniohexanoate

Y-05460M-A