1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil

Base Information

Chemical Name:1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil
CAS No.:648414-61-3
Molecular Formula:C₂₄H₂₅FN₂O₄
Molecular Weight:424.472
Hs Code.:

Synonyms:1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil

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Chemical Property of 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil

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Technology Process of 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil

There total 7 articles about 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil 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: 42.0%

: 114826-94-7
(1S,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol

: 61251-77-2
3-benzoyl-5-fluorouracil

: 648414-61-3
1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil

: 2-((1R,3S,4R)-3-Benzyloxy-4-benzyloxymethyl-cyclopentyloxy)-5-fluoro-3H-pyrimidin-4-one

Guidance literature:: (1S,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol; 3-benzoyl-5-fluorouracil; With di-isopropyl azodicarboxylate; triphenylphosphine; In acetonitrile; at -40 - 20 ℃; for 16h;

With sodium hydroxide; In methanol; at 20 ℃;
DOI:10.1055/s-2003-41455

Reference yield:

: 191480-69-0
(3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene

: 648414-61-3
1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil

Guidance literature:: Multi-step reaction with 4 steps

1.1: Hg(F₃CC(O)O)2 / H₂O

2.1: PPh₃; DIAD / diethyl ether / 20 °C

3.1: 3.70 g / NaOH / methanol / 20 °C

4.1: PPh₃; DIAD / acetonitrile / 16 h / -40 - 20 °C

4.2: 42 percent / aq. NaOH / methanol / 20 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; Hg(II) trifluoroacetate; triphenylphosphine; In methanol; diethyl ether; water; acetonitrile; 2.1: Mitsunobu-inversion / 4.1: Mitsunobu reaction;
DOI:10.1055/s-2003-41455

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 648414-61-3
1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-fluorouracil

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: tetrahydrofuran / 2 h / -40 °C

2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C

2.2: 8.20 g / aq. NaOH; H₂O₂ / diethyl ether; tetrahydrofuran / 12 h / 0 °C

3.1: NaH / tetrahydrofuran / 1 h / 20 °C

3.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C

4.1: Hg(F₃CC(O)O)2 / H₂O

5.1: PPh₃; DIAD / acetonitrile / 16 h / -40 - 20 °C

5.2: 42 percent / aq. NaOH / methanol / 20 °C

With di-isopropyl azodicarboxylate; Hg(II) trifluoroacetate; sodium hydride; triphenylphosphine; diisopinocampheylborane; In tetrahydrofuran; water; acetonitrile; 5.1: Mitsunobu reaction;
DOI:10.1055/s-2003-41455