(2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester

Base Information

Chemical Name:(2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester
CAS No.:159614-52-5
Molecular Formula:C₂₂H₃₃Cl₄NO₃
Molecular Weight:501.321
Hs Code.:

Synonyms:(2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester

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Chemical Property of (2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester

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Technology Process of (2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester

There total 7 articles about (2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl 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: 50.0%

: 115887-59-7
(1S,2R)-N-methylephedrine propionate derived E silyl ketene acetal

: 159614-51-4
6,6,7,7-tetrachlorooctanal

: (2S,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester

: 159614-52-5
(2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 ℃; for 2h; Yields of byproduct given;
DOI:10.1021/ja00097a019

Reference yield:

: 63478-76-2
1-hydroxy-6-heptyne

: 159614-52-5
(2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

2: 1.) LDA / 1.) THF, -78 deg C, 0.5 h, 2.) THF, overnight

3: 60 percent / sulfuryl chloride / benzene; CH₂Cl₂ / 96 h / Heating

4: 81 percent / 1.5 N aq. NaOH / methanol / 10 h / Ambient temperature

5: 71 percent / Dess-Martin reagent / CH₂Cl₂ / 4 h

6: 50 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

With sodium hydroxide; sulfuryl dichloride; titanium tetrachloride; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In methanol; dichloromethane; benzene;
DOI:10.1021/ja00097a019

Reference yield:

: 1002-36-4
hep-2-yn-1-ol

: 159614-52-5
(2R,3R)-8,8,9,9-Tetrachloro-3-hydroxy-2-methyl-decanoic acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 83 percent / 1,2-diaminoethane, Li, potassium tert-butoxide / 3 h

2: 91 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

3: 1.) LDA / 1.) THF, -78 deg C, 0.5 h, 2.) THF, overnight

4: 60 percent / sulfuryl chloride / benzene; CH₂Cl₂ / 96 h / Heating

5: 81 percent / 1.5 N aq. NaOH / methanol / 10 h / Ambient temperature

6: 71 percent / Dess-Martin reagent / CH₂Cl₂ / 4 h

7: 50 percent / TiCl₄ / CH₂Cl₂ / 2 h / -78 °C

With sodium hydroxide; sulfuryl dichloride; potassium tert-butylate; titanium tetrachloride; lithium; Dess-Martin periodane; ethylenediamine; triethylamine; lithium diisopropyl amide; In methanol; dichloromethane; benzene;
DOI:10.1021/ja00097a019