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

Base Information

• Chemical Name: 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
• CAS No.: 264128-13-4
• Molecular Formula: C₅₃H₅₇N₅O₁₃
• Molecular Weight: 972.061
• Mol file: 264128-13-4.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 13 articles about 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 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:

Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (264128-12-3) → 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 (264128-13-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)02209-1

Reference yield:

1,2,3,4,6‐Pentaacetyl α/β‐L‐mannopyranoside (153830-26-3) → 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 (264128-13-4)

Guidance literature:

Multi-step reaction with 9 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

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; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation / 3: Cyclization / 4: Alkylation / 5: Oxidation / 6: Substitution / 7: Hydrolysis / 8: Tosylation / 9: Substitution;

DOI:10.1016/S0040-4039(99)02209-1

Reference yield:

5'-O-trityluridine (6554-10-5) → 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 (264128-13-4)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; formic acid; sodium azide; trifluoromethylsulfonic anhydride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Alkylation / 2: detritylation / 3: Substitution / 4: Hydrolysis / 5: Tosylation / 6: Substitution;

DOI:10.1016/S0040-4039(99)02209-1

upstream raw materials:

Toluene-4-sulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

1,2,3,4,6‐Pentaacetyl α/β‐L‐mannopyranoside

5'-O-trityluridine

uridine

Downstream raw materials:

N-{(2S,3S,4R,5R,6S)-4,5-Bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-3-hydroxy-tetrahydro-pyran-2-ylmethyl}-acetamide

Octadecyl-carbamic acid (2S,3S,4R,5R,6S)-2-(acetylamino-methyl)-4,5-bis-benzyloxy-6-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-pyran-3-yl ester

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