Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester

Base Information

Chemical Name:Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester
CAS No.:149454-99-9
Molecular Formula:C₂₆H₂₇N₃O₈
Molecular Weight:509.516
Hs Code.:

Synonyms:Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester

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Chemical Property of Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester

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Technology Process of Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester

There total 17 articles about Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester 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: 50.0%

: 149454-95-5
Acetic acid (1R,4R,5R)-4,5-bis-benzyloxy-2-nitro-cyclopent-2-enylmethyl ester

: 10457-14-4
O,O'-bis-(trimethylsilyl)uracil

: 149454-99-9
Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester

Guidance literature:: With cesium fluoride; In N,N-dimethyl-formamide; at 25 ℃; for 1h;
DOI:10.1248/cpb.41.636 DOI:10.1016/S0040-4020(01)89611-3

Reference yield:

: 149454-89-7
methyl 2,3-di-O-benzyl-β-D-arabinopyranoside

: 149454-99-9
Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) (COCl)2, DMSO; 2.) triethylamine / 1.) CH₂Cl₂, -40 deg C, 6 h; 2.) CH₂Cl₂, 25 deg C, 30 min

2: KF, 18-crown-6 / dimethylformamide / 0.5 h / 25 °C

3: p-toluenesulfonic acid monohydrate / 25 °C

4: NaBH₄ / ethanol / 1 h / 25 °C

5: 57 percent / concd. HCl / acetic acid / 30 °C

6: 86 percent / CsF / dimethylformamide / 3 h / 25 °C

7: p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

8: 50 percent / CsF / dimethylformamide / 1 h / 25 °C

With hydrogenchloride; potassium fluoride; sodium tetrahydroborate; oxalyl dichloride; 18-crown-6 ether; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; cesium fluoride; In ethanol; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89611-3

Reference yield:

: (3S,4R,5R)-3,4-Bis-benzyloxy-5-nitromethyl-tetrahydro-pyran-2-ol

: 149454-99-9
Acetic acid (1R,2R,3R,4R,5S)-2,3-bis-benzyloxy-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-nitro-cyclopentylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / CsF / dimethylformamide / 3 h / 25 °C

2: p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

3: 50 percent / CsF / dimethylformamide / 1 h / 25 °C

With toluene-4-sulfonic acid; cesium fluoride; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89611-3