5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine

Base Information

Chemical Name:5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine
CAS No.:156386-25-3
Molecular Formula:C₃₃H₃₅N₃O₈
Molecular Weight:601.656
Hs Code.:

Synonyms:5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine

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Chemical Property of 5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine

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Technology Process of 5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine

There total 7 articles about 5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine 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: 91.0%

: 156386-24-2
1-<5'-O-MMTr-2'-C,3'-O-dimethylsilamethylidene-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S),10-N-(R)-methyl-9,10-isoxazolidine)>-β-D-ribofuranosyl>thymine

: 156386-25-3
5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine

Guidance literature:: With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; 5 deg C to RT;
DOI:10.1016/S0040-4020(01)85027-4

Reference yield:

: 86872-09-5
1-(5'-O-(monomethoxytrityl)-β-D-ribofuranosyl)thymine

: 156386-25-3
5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine

Guidance literature:: Multi-step reaction with 6 steps

1: 33 percent / imidazole / dimethylformamide / Ambient temperature

2: CrO₃/pyridine/Ac₂O / CH₂Cl₂ / Ambient temperature

3: pyridine / 48 h / 0 - 5 °C

4: 67 percent / NH₄F / methanol / 0 - 5 °C

5: 70 percent / pyridine / 0 - 5 °C

6: 91 percent / KF, 30percent H₂O₂, KHCO₃ / methanol; tetrahydrofuran / 5 deg C to RT

With pyridine; 1H-imidazole; chromium(VI) oxide; ammonium fluoride; potassium fluoride; dihydrogen peroxide; acetic anhydride; potassium hydrogencarbonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)85027-4

Reference yield:

: 156386-23-1
5'-O-MMTr-2'-deoxy-2'-dehydro-(E)-(N-methyloximino)-5-methyluridine

: 156386-25-3
5'-O-MMTr-2'-deoxy-2'-dehydro-spiro<2'(S),11-(7(S)-hydroxy-10-N-(R)-methyl-9,10-isoxazolidine)>thymidine

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / pyridine / 0 - 5 °C

2: 91 percent / KF, 30percent H₂O₂, KHCO₃ / methanol; tetrahydrofuran / 5 deg C to RT

With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; pyridine; methanol;
DOI:10.1016/S0040-4020(01)85027-4