3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine

Base Information

Chemical Name:3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine
CAS No.:246538-23-8
Molecular Formula:C₃₃H₃₅N₃O₆
Molecular Weight:569.657
Hs Code.:

Synonyms:3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine

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Chemical Property of 3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine

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Technology Process of 3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine

There total 12 articles about 3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine 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:

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

: 246538-23-8
3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine

Guidance literature:: Multi-step reaction with 7 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

4.1: 91 percent / AgNO₃ / pyridine / 34 h / 55 °C

5.1: 4.83 g / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

6.1: 3.28 g / DMAP / pyridine / 5 h / 20 °C

7.1: 1.51 g / H₂; Et₃N / ethanol / 22 h / 20 °C / 2585.74 Torr

With dmap; lithium aluminium tetrahydride; hydrogen; sodium carbonate; silver nitrate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; In tetrahydrofuran; pyridine; diethyl ether; ethanol; water; 1.1: Acylation / 2.1: Oxidation / 3.1: Metallation / 3.2: Reformatsky reaction / 4.1: tritylation / 5.1: Reduction / 6.1: Tosylation / 7.1: Hydrogenolysis;
DOI:10.1080/15257770008033851

Reference yield:

: Toluene-4-sulfonic acid (S)-3-[(2S,3S,5R)-3-benzyloxycarbonylamino-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-propyl ester

: 246538-23-8
3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine

Guidance literature:: With hydrogen; triethylamine; In ethanol; at 20 ℃; for 22h; under 2585.74 Torr;
DOI:10.1080/15257770008033851

Reference yield:

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

: 246538-23-8
3'-C-amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3-N,5'(R)-C-ethylenethymidine

Guidance literature:: Multi-step reaction with 8 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

5.1: 91 percent / AgNO₃ / pyridine / 34 h / 55 °C

6.1: 4.83 g / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

7.1: 3.28 g / DMAP / pyridine / 5 h / 20 °C

8.1: 1.51 g / H₂; Et₃N / ethanol / 22 h / 20 °C / 2585.74 Torr

With dmap; lithium aluminium tetrahydride; hydrogen; sodium carbonate; silver nitrate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; water; 1.1: Reduction / 2.1: Acylation / 3.1: Oxidation / 4.1: Metallation / 4.2: Reformatsky reaction / 5.1: tritylation / 6.1: Reduction / 7.1: Tosylation / 8.1: Hydrogenolysis;
DOI:10.1080/15257770008033851