methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate

Base Information

Chemical Name:methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate
CAS No.:229027-69-4
Molecular Formula:C₃₄H₃₅N₃O₈
Molecular Weight:613.667
Hs Code.:

Synonyms:methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate

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Chemical Property of methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate

Chemical Property:

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Technology Process of methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate

There total 8 articles about methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate 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: 92.0%

: 20924-05-4
thymidyl acetic acid

: 229027-68-3
methyl (S)-4-(4,4'-dimethoxytrityloxy)-L-prolinate

: 229027-69-4
methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;
DOI:10.1080/15257779908043093

Reference yield:

: 126407-76-9
(2S,4R)-N-(allyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

: 229027-69-4
methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.51 g / chlorotrimethylsilane / 48 h

2: 66 percent / triphenylphosphine; diethyl azodicarboxylate / dimethylformamide / 16 h / 0 °C

3: 85 percent / KOtBu / methanol / 2 h

4: 85 percent / pyridine; tetrabutylammonium iodide; 4-(dimethylamino)pyridine / 16 h / 50 °C

5: 85 percent / acetic acid; tributyltin hydride / dichlorobis(triphenylphosphine)palladium(II) / CH₂Cl₂ / 0.5 h

6: 92 percent / 1-hydroxybenzotriazole; N,N'-dicyclohexylcarbodiimide / dimethylformamide

With pyridine; dmap; chloro-trimethyl-silane; potassium tert-butylate; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; bis-triphenylphosphine-palladium(II) chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Esterification / 3: Zemplen deacylation / 4: Etherification / 5: deprotection / 6: Acylation;
DOI:10.1080/15257779908043093

Reference yield:

: 46122-47-8
(2S,4R)-O-acetyl-4-hydroxyproline

: 229027-69-4
methyl (S)-4-(4,4'-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-prolinate

Guidance literature:: Multi-step reaction with 8 steps

1: aq. HCl / 3 h / Heating

2: Na₂CO₃; NaHCO₃ / dioxane; H₂O / 2 h / pH 9

3: 1.51 g / chlorotrimethylsilane / 48 h

4: 66 percent / triphenylphosphine; diethyl azodicarboxylate / dimethylformamide / 16 h / 0 °C

5: 85 percent / KOtBu / methanol / 2 h

6: 85 percent / pyridine; tetrabutylammonium iodide; 4-(dimethylamino)pyridine / 16 h / 50 °C

7: 85 percent / acetic acid; tributyltin hydride / dichlorobis(triphenylphosphine)palladium(II) / CH₂Cl₂ / 0.5 h

8: 92 percent / 1-hydroxybenzotriazole; N,N'-dicyclohexylcarbodiimide / dimethylformamide

With pyridine; hydrogenchloride; dmap; chloro-trimethyl-silane; potassium tert-butylate; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; sodium carbonate; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Deacetylation / 2: Acylation / 3: Esterification / 4: Esterification / 5: Zemplen deacylation / 6: Etherification / 7: deprotection / 8: Acylation;
DOI:10.1080/15257779908043093