1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine

Base Information

Chemical Name:1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine
CAS No.:133713-95-8
Molecular Formula:C₁₈H₂₂N₂O₅
Molecular Weight:346.383
Hs Code.:

Synonyms:1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine

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Chemical Property of 1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine

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Technology Process of 1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine

There total 6 articles about 1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine 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: 72.0%

: 445249-30-9
1-{3-[(p-anisyloxy)methyl]-5-O-benzyl-2,3-dideoxy-β-D-erythro-pentofuranosyl}thymine

: 133713-95-8
1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine

Guidance literature:: With ammonium cerium(IV) nitrate; water; In acetonitrile; for 0.0833333h;
DOI:10.1021/jm021108n

Reference yield:

: 65-71-4,28806-14-6,691841-57-3
thymin

: 133713-95-8
1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine

Guidance literature:: Multi-step reaction with 6 steps

1: trimethylsilyl chloride; pyridine / Heating

2: trimethylsilyl triflate / 1,2-dichloro-ethane / 5 h / 20 °C

3: 592 mg / NH₃ / methanol / 15 h / 20 °C

4: DMAP / acetonitrile / 1.5 h / 0 °C

5: 3.98 g / 2,2'-azobis(2-methyl-propionitrile); tri-n-butyltinhydride / toluene / 1 h / 95 - 100 °C

6: 72 percent / ceric ammonium nitrate; H₂O / acetonitrile / 0.08 h

With pyridine; dmap; chloro-trimethyl-silane; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; ammonia; water; tri-n-butyl-tin hydride; In methanol; 1,2-dichloro-ethane; toluene; acetonitrile; 2: Vorbrueggen-type coupling;
DOI:10.1021/jm021108n

Reference yield:

: 7288-28-0
2,4-bis(trimethylsiloxy)-5-methylpyrimidine

: 133713-95-8
1-[5-O-benzyl-2,3-dideoxy-3-(hydroxymethyl)-β-D-erythro-pentofuranosyl]thymine

Guidance literature:: Multi-step reaction with 5 steps

1: trimethylsilyl triflate / 1,2-dichloro-ethane / 5 h / 20 °C

2: 592 mg / NH₃ / methanol / 15 h / 20 °C

3: DMAP / acetonitrile / 1.5 h / 0 °C

4: 3.98 g / 2,2'-azobis(2-methyl-propionitrile); tri-n-butyltinhydride / toluene / 1 h / 95 - 100 °C

5: 72 percent / ceric ammonium nitrate; H₂O / acetonitrile / 0.08 h

With dmap; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; ammonia; water; tri-n-butyl-tin hydride; In methanol; 1,2-dichloro-ethane; toluene; acetonitrile; 1: Vorbrueggen-type coupling;
DOI:10.1021/jm021108n