3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine

Base Information

Chemical Name:3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine
CAS No.:246538-18-1
Molecular Formula:C₂₂H₂₇N₃O₈
Molecular Weight:461.472
Hs Code.:

Synonyms:3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine

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Chemical Property of 3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine

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Technology Process of 3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine

There total 4 articles about 3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine 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: 61.9%

: 105-36-2
ethyl bromoacetate

: 246538-34-1
[(2S,3S,5R)-2-Formyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

: 246538-18-1
3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine

Guidance literature:: ethyl bromoacetate; With zinc; In tetrahydrofuran; at 45 ℃; for 0.5h;

[(2S,3S,5R)-2-Formyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-carbamic acid benzyl ester; In tetrahydrofuran; at 42 - 45 ℃; for 20h;
DOI:10.1080/15257770008033851

Reference yield:

: 52450-18-7
3'-amino-3'-deoxythymidine

: 246538-18-1
3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 27.3 g / Na₂CO₃ / H₂O / 0 - 20 °C

2.1: 88 percent / DCC; DMSO; TFA / diethyl ether; pyridine / 5 h / 20 °C

3.1: Zn powder / tetrahydrofuran / 0.5 h / 45 °C

3.2: 61.9 percent / tetrahydrofuran / 20 h / 42 - 45 °C

With sodium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; In tetrahydrofuran; pyridine; diethyl ether; water; 1.1: Acylation / 2.1: Oxidation / 3.1: Metallation / 3.2: Reformatsky reaction;
DOI:10.1080/15257770008033851

Reference yield:

: 30516-87-1,399024-19-2
3'-azido-2',3'-deoxythymidine

: 246538-18-1
3'-C-carbobenzyloxyamino-3'-deoxy-5'(R,S)-C-ethoxycarbonylmethylthymidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: H₂ / Pd/C / methanol / 4 h / 20 °C / 2844.31 Torr

2.1: 27.3 g / Na₂CO₃ / H₂O / 0 - 20 °C

3.1: 88 percent / DCC; DMSO; TFA / diethyl ether; pyridine / 5 h / 20 °C

4.1: Zn powder / tetrahydrofuran / 0.5 h / 45 °C

4.2: 61.9 percent / tetrahydrofuran / 20 h / 42 - 45 °C

With hydrogen; sodium carbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; water; 1.1: Reduction / 2.1: Acylation / 3.1: Oxidation / 4.1: Metallation / 4.2: Reformatsky reaction;
DOI:10.1080/15257770008033851