1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione
CAS No.:264128-14-5
Molecular Formula:C₅₃H₅₉N₃O₁₃
Molecular Weight:946.064
Hs Code.:

1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione

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Chemical Property of 1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione

There total 14 articles about 1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione 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:

: 264128-13-4
1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Azidomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione

: 264128-14-5
1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione

Guidance literature:: With trimethylphosphane; In tetrahydrofuran; ethanol; water;
DOI:10.1016/S0040-4039(99)02209-1

Reference yield:

: 153830-26-3
1,2,3,4,6‐Pentaacetyl α/β‐L‐mannopyranoside

: 264128-14-5
1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 10 steps

1: 76 percent / BF₃*OEt₂ / CH₂Cl₂ / 20 °C

2: NaOMe / methanol

3: TsOH / dimethylformamide / 70 °C

4: 95 percent / NBu₄I; NaH / tetrahydrofuran

5: 87 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / -78 - 20 °C

6: 53 percent / Tf₂O / CH₂Cl₂ / -78 - -20 °C

7: H₂O; AcOH / 50 °C

8: pyridine

9: NaN₃ / dimethylformamide

10: PMe₃ / tetrahydrofuran; ethanol; H₂O

With pyridine; sodium azide; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; water; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; trimethylphosphane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation / 3: Cyclization / 4: Alkylation / 5: Oxidation / 6: Substitution / 7: Hydrolysis / 8: Tosylation / 9: Substitution / 10: Reduction;
DOI:10.1016/S0040-4039(99)02209-1

Reference yield:

: 6554-10-5
5'-O-trityluridine

: 264128-14-5
1-[(2R,3R,4R,5R)-5-((2S,3R,4R,5S,6S)-6-Aminomethyl-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yloxymethyl)-3,4-bis-benzyloxymethoxy-tetrahydro-furan-2-yl]-3-benzyloxymethyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 7 steps

1: 40 percent / NaH; NBu₄I / dimethylformamide

2: 100 percent / HCOOH / acetonitrile / 0.25 h / 20 °C

3: 53 percent / Tf₂O / CH₂Cl₂ / -78 - -20 °C

4: H₂O; AcOH / 50 °C

5: pyridine

6: NaN₃ / dimethylformamide

7: PMe₃ / tetrahydrofuran; ethanol; H₂O

With pyridine; formic acid; sodium azide; trifluoromethylsulfonic anhydride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Alkylation / 2: detritylation / 3: Substitution / 4: Hydrolysis / 5: Tosylation / 6: Substitution / 7: Reduction;
DOI:10.1016/S0040-4039(99)02209-1