1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil

Base Information

Chemical Name:1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil
CAS No.:648414-67-9
Molecular Formula:C₂₆H₂₇BrN₂O₄
Molecular Weight:511.415
Hs Code.:

Synonyms:1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil

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Chemical Property of 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil

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Technology Process of 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil

There total 8 articles about 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil 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: 53.0%

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

: 185816-33-5
3-benzoyl-5-(2-bromovinyl)uracil

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

: 648414-67-9
1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil

Guidance literature:: (1S,3S,4R)-3-benzyloxy-4-benzyloxymethylcyclopentan-1-ol; 3-benzoyl-5-(2-bromovinyl)uracil; 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:

: 3587-60-8
Benzyloxymethyl chloride

: 648414-67-9
1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil

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: 53 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

Reference yield:

: 39939-07-6
5-(benzyloxymethyl)cyclopentadiene

: 648414-67-9
1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)-5-[(E)-bromovinyl]uracil

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 8.20 g / aq. NaOH; H₂O₂ / diethyl ether; tetrahydrofuran / 12 h / 0 °C

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

2.2: 92 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C

3.1: Hg(F₃CC(O)O)2 / H₂O

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

4.2: 53 percent / aq. NaOH / methanol / 20 °C

With di-isopropyl azodicarboxylate; Hg(II) trifluoroacetate; sodium hydride; triphenylphosphine; diisopinocampheylborane; In tetrahydrofuran; water; acetonitrile; 4.1: Mitsunobu reaction;
DOI:10.1055/s-2003-41455