(+)-(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxooxazole

Base Information

• Chemical Name: (+)-(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxooxazole
• CAS No.: 133056-49-2
• Molecular Formula: C₂₄H₂₅NO₅
• Molecular Weight: 407.466
• Mol file: 133056-49-2.mol

Synonyms:

Chemical Property of (+)-(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxooxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxooxazole

There total 3 articles about (+)-(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxooxazole 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:

1,4,5-Trimethoxynaphthalene-2-carbonitrile (123796-58-7) → (+)-(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxooxazole (133056-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / potassium hydroxide / 2-methyl-propan-2-ol / 1.5 h / Heating

2: 1.) triethyloxonium tetrafluoroborate / 1.) 1,2-dichloroethane, r.t., 24h, 2.) reflux, 48h

With potassium hydroxide; triethyloxonium fluoroborate; In tert-butyl alcohol;

DOI:10.1039/P19910000845

Reference yield:

(1S,2S)-2-amino-3-methoxy-1-phenyl-1-propanol (51594-34-4) + 1,4,5-Trimethoxynaphthalene-2-carboxamide (133056-48-1) → (+)-(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxooxazole (133056-49-2)

Guidance literature:

With triethyloxonium fluoroborate; Yield given. Multistep reaction; 1.) ClCH₂CH₂Cl, 25 deg C, 24 h, 2.) reflux, 48 h;

DOI:10.1039/c39900000894

Reference yield:

(+)-(4S,5S)-2-(1-hydroxy-4,5-dimethoxy-2-naphthyl)-4-(methoxymethyl)-5-phenyl-4,5-dihydrooxazole (133056-52-7) + methyl iodide (74-88-4) → (+)-(4S,5S)-4-(Methoxymethyl)-5-phenyl-2-(1,4,5-trimethoxy-2-naphthyl)-4,5-dihydroxooxazole (133056-49-2)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, 60 deg C, 1h, 2.) reflux, 18h;

DOI:10.1039/P19910000845

upstream raw materials:

(1S,2S)-2-amino-3-methoxy-1-phenyl-1-propanol

1,4,5-Trimethoxynaphthalene-2-carboxamide

(+)-(4S,5S)-2-(1-hydroxy-4,5-dimethoxy-2-naphthyl)-4-(methoxymethyl)-5-phenyl-4,5-dihydrooxazole

methyl iodide

Downstream raw materials:

(+)-(R,4S,5S)-2-<1-<2-(1,3-Dioxan-2-yl)-4,6-dimethoxyphenyl>-4,5-dimethoxy-2-naphthyl>-4-(methoxymethyl)-5-phenyl-4,5-dihydrooxazole

(+)-(S,4S,5S)-2-<1-<2-(1,3-Dioxan-2-yl)-4,6-dimethoxyphenyl>-4,5-dimethoxy-2-naphthyl>-4-(methoxymethyl)-5-phenyl-4,5-dihydroxooxazole

(+)-(4S,5S)-2-(1-hydroxy-4,5-dimethoxy-2-naphthyl)-4-(methoxymethyl)-5-phenyl-4,5-dihydrooxazole

(+)-(R,4S,5S)-4,5-dihydro-2-<1<2-(1,3-dioxolan-2-yl)-4,6-dimethoxyphenyl>-4,5-dimethoxy-2-naphthyl>-4-methoxymethyl-5-phenyloxazole

Refernces

• 1、 Rizzacasa, Mark A.,Sargent, Melvyn V.. "Synthetic Approaches to the Alkaloids of the Ancistrocladaceae: (-)-O-Methylancistrocladine and (+)-O-Methylhamatine". . p. 894 - 896. Retrieved 2007/10/02.