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

Base Information

• Chemical Name: 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• CAS No.: 264128-11-2
• Molecular Formula: C₅₃H₅₈N₂O₁₄
• Molecular Weight: 947.049
• Mol file: 264128-11-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-2-yl]-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:

3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,4aS,6S,7R,8R,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (264128-10-1) → 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (264128-11-2)

Guidance literature:

With water; acetic acid; at 50 ℃;

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

Reference yield:

1,2,3,4,6‐Pentaacetyl α/β‐L‐mannopyranoside (153830-26-3) → 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (264128-11-2)

Guidance literature:

Multi-step reaction with 7 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

With 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;

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

Reference yield:

5'-O-trityluridine (6554-10-5) → 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,3R,4R,5S,6S)-3,4-bis-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (264128-11-2)

Guidance literature:

Multi-step reaction with 4 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

With formic acid; 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;

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

upstream raw materials:

3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3,4-bis-benzyloxymethoxy-5-((2S,4aS,6S,7R,8R,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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

5'-O-trityluridine

uridine

Downstream 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-[(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

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

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