(2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Base Information

Chemical Name:(2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester
CAS No.:159526-65-5
Molecular Formula:C₂₆H₃₀ClNO₇Si
Molecular Weight:532.065
Hs Code.:

Synonyms:(2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

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Chemical Property of (2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

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Technology Process of (2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

There total 8 articles about (2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: (S)-3-(4-Acetoxy-3-chloro-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-propionic acid methyl ester

: 159526-65-5
(2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

: (2S,3S)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Guidance literature:: With 2,4,6-trimethyl-pyridine; In dichloromethane; at 0 ℃; for 0.166667h; Yield given. Yields of byproduct given;
DOI:10.1016/S0040-4039(00)73315-6

Reference yield:

: 39739-09-8
methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoate

: 159526-65-5
(2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / SO₂Cl₂ / diethyl ether / 0.25 h / Ambient temperature

2: 96 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

3: 98 percent / NBS, AIBN / CCl₄ / 6 h / Heating

4: 76 percent / AgNO₃ / acetone; H₂O / 3 h / Ambient temperature

5: 2,4,6-collidine / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); silver nitrate; In tetrachloromethane; diethyl ether; dichloromethane; water; acetone;
DOI:10.1016/S0040-4039(00)73315-6

Reference yield:

: 22509-74-6
N-ethoxycarbonylphthalimide

: 159526-65-5
(2S,3R)-3-(4-Acetoxy-3-chloro-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / NaOH / 0.5 h / 0 °C

2: 83 percent / H₂SO₄ / 6 h / Heating

3: 94 percent / SO₂Cl₂ / diethyl ether / 0.25 h / Ambient temperature

4: 96 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

5: 98 percent / NBS, AIBN / CCl₄ / 6 h / Heating

6: 76 percent / AgNO₃ / acetone; H₂O / 3 h / Ambient temperature

7: 2,4,6-collidine / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; sodium hydroxide; N-Bromosuccinimide; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); sulfuric acid; silver nitrate; In tetrachloromethane; diethyl ether; dichloromethane; water; acetone;
DOI:10.1016/S0040-4039(00)73315-6