methyl 4-(N⁶-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate

Base Information

Chemical Name:methyl 4-(N⁶-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate
CAS No.:84955-88-4
Molecular Formula:C₂₆H₂₈N₆O₁₀
Molecular Weight:584.543
Hs Code.:

methyl 4-(N<sup>6</sup>-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate

Synonyms:

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Chemical Property of methyl 4-(N⁶-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate

Chemical Property:

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Technology Process of methyl 4-(N⁶-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate

There total 10 articles about methyl 4-(N⁶-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate 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:

: 13013-02-0
methyl 4-nitrobutyrate

: 84955-88-4,94902-95-1,94902-96-2
methyl 4-(N⁶-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate

Guidance literature:: Multi-step reaction with 6 steps

1: 2) oxalic acid dihydrate / 1) KF / 1) 48 h; 2) MeOH, 30 min

2: 65 percent / acetic anhydride, 4-dimethylaminopyridine / dioxane / 0.33 h / Ambient temperature

3: 93 percent / 1) NaBH₄; 2) 10 percent H₂SO₄ / ethanol; H₂O; dioxane / 0.33 h / 0 °C

4: H₂O; acetic acid / 1.5 h / Heating

5: 4-dimethylaminopyridine / dioxane / 0.33 h / Ambient temperature

6: 1) N,O-bis(trimethylsilyl)acetamide; 2) trimethylsilyl triflate / 1) CH₃CN, reflux, 15 min; 2) CH₃CN, reflux, 6 h

With dmap; sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; oxalic acid; acetic anhydride; potassium fluoride; In 1,4-dioxane; ethanol; water; acetic acid;
DOI:10.1248/cpb.32.2915

Reference yield:

: 94834-38-5
1-(5,6-dideoxy-6-nitro-2,3-O-isopropylidene-β-D-ribo-hexofuranosyl)uracil

: 84955-88-4,94902-95-1,94902-96-2
methyl 4-(N⁶-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate

Guidance literature:: Multi-step reaction with 4 steps

1: KF / dimethylformamide / 6 h / Ambient temperature

2: H₂O; acetic acid / 1.5 h / Heating

3: 4-dimethylaminopyridine / dioxane / 0.33 h / Ambient temperature

4: 1) N,O-bis(trimethylsilyl)acetamide; 2) trimethylsilyl triflate / 1) CH₃CN, reflux, 15 min; 2) CH₃CN, reflux, 6 h

With dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; potassium fluoride; In 1,4-dioxane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1248/cpb.32.2915

Reference yield:

: 94834-35-2,94834-36-3
9-(6-Deoxy-6-nitro-2,3-O-isopropylidene-β-D-allofuranosyl)uracil

: 84955-88-4,94902-95-1,94902-96-2
methyl 4-(N⁶-benzoyl-2',3'-di-O-acetyladenosin-5'-yl)-4-nitrobutanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 1) acetic anhydride, 4-dimethylaminopyridine; 2) NaBH₄; 10 percent H₂SO₄ / 1) dioxane, 20 deg C, 20 min; 2) dioxane, H₂O, EtOH, 20 min

2: KF / dimethylformamide / 6 h / Ambient temperature

3: H₂O; acetic acid / 1.5 h / Heating

4: 4-dimethylaminopyridine / dioxane / 0.33 h / Ambient temperature

5: 1) N,O-bis(trimethylsilyl)acetamide; 2) trimethylsilyl triflate / 1) CH₃CN, reflux, 15 min; 2) CH₃CN, reflux, 6 h

With dmap; sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic anhydride; potassium fluoride; In 1,4-dioxane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1248/cpb.32.2915