(2S,3R)-methyl 2-phthalimido-3-(^tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate

Base Information

• Chemical Name: (2S,3R)-methyl 2-phthalimido-3-(^tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate
• CAS No.: 159379-70-1
• Molecular Formula: C₂₄H₂₈ClNO₆Si
• Molecular Weight: 490.028

Synonyms:(2S,3R)-methyl 2-phthalimido-3-(^tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate

Chemical Property of (2S,3R)-methyl 2-phthalimido-3-(^tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate

Chemical Property:

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Technology Process of (2S,3R)-methyl 2-phthalimido-3-(^tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate

There total 9 articles about (2S,3R)-methyl 2-phthalimido-3-(^tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate 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: 71.0%

(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 (159526-65-5) → (2S,3R)-methyl 2-phthalimido-3-(tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate (159379-70-1)

Guidance literature:

With sodium methylate; In methanol; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)73315-6

Reference yield:

methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoate (39739-09-8) → (2S,3R)-methyl 2-phthalimido-3-(tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate (159379-70-1)

Guidance literature:

Multi-step reaction with 6 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

6: 71 percent / NaOMe / methanol / 0.08 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); sodium methylate; silver nitrate; In methanol; tetrachloromethane; diethyl ether; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(00)73315-6

Reference yield:

N-ethoxycarbonylphthalimide (22509-74-6) → (2S,3R)-methyl 2-phthalimido-3-(tbutyldimethylsilyloxy)-3-(3'-chloro-4'-hydroxy phenyl)propionate (159379-70-1)

Guidance literature:

Multi-step reaction with 8 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

8: 71 percent / NaOMe / methanol / 0.08 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; sodium hydroxide; N-Bromosuccinimide; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); sulfuric acid; sodium methylate; silver nitrate; In methanol; tetrachloromethane; diethyl ether; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(00)73315-6

upstream raw materials:

(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

methyl (S)-2-(1,3-dioxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoate

N-ethoxycarbonylphthalimide

N-phthaloyl-L-tyrosine

Downstream raw materials:

C₅₂H₆₄Cl₂N₂O₁₄Si₂

C₅₂H₆₆Cl₂N₂O₁₄Si₂

C₅₅H₇₀Cl₂N₂O₁₃Si₂

C₅₃H₆₈Cl₂N₂O₁₄Si₂

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