2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:153693-57-3
Molecular Formula:C₂₄H₃₅IO₁₀
Molecular Weight:610.44
Hs Code.:

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Synonyms:2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 11 articles about 2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester 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: 84.0%

: 153693-41-5
2-((tert-butyldiphenylsilyloxy)methyl)-5-<(4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-α-L-mannopyranosyl)oxy>-3,4-dimethoxy-6-iodotoluene

: 153693-57-3
2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 4h;
DOI:10.1021/ja00084a018

Reference yield:

: 115592-74-0,115650-45-8,127761-05-1
4-Hydroxy-5-iod-2,3-dimethoxy-6-methyl-benzoesaeuremethylester

: 153693-57-3
2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: DIBAL / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) 25 deg C, 5 min

2: imidazole / dimethylformamide / 2 h / 65 °C

3: 1.) 2,6-di-tert-butyl-4-methylpyridine, 2.) (Bu₃Sn)2O

4: 84 percent / TBAF / tetrahydrofuran / 4 h / 25 °C

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; bis(tri-n-butyltin)oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00084a018

Reference yield:

: 3282-30-2
pivaloyl chloride

: 153693-57-3
2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / pyridine / 6 h / 60 °C

2: 92 percent / mCPBA / CH₂Cl₂ / 0.83 h / -78 - 0 °C

3: 1.) 2,6-di-tert-butyl-4-methylpyridine, 2.) (Bu₃Sn)2O

4: 84 percent / TBAF / tetrahydrofuran / 4 h / 25 °C

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; bis(tri-n-butyltin)oxide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00084a018