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

Base Information

• Chemical Name: 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
• CAS No.: 264128-15-6
• Molecular Formula: C₅₅H₆₁N₃O₁₄
• Molecular Weight: 988.101
• Mol file: 264128-15-6.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 15 articles about 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 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:

1,2,3,4,6‐Pentaacetyl α/β‐L‐mannopyranoside (153830-26-3) → 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 (264128-15-6)

Guidance literature:

Multi-step reaction with 11 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

11: HATU; DIPEA / 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; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 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 / 11: Acetylation;

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

Reference yield:

5'-O-trityluridine (6554-10-5) → 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 (264128-15-6)

Guidance literature:

Multi-step reaction with 8 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

8: HATU; DIPEA / dimethylformamide

With pyridine; formic acid; sodium azide; trifluoromethylsulfonic anhydride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 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 / 8: Acetylation;

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

Reference yield:

uridine (58-96-8) → 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 (264128-15-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 94 percent / DMAP; pyridine

2: 40 percent / NaH; NBu₄I / dimethylformamide

3: 100 percent / HCOOH / acetonitrile / 0.25 h / 20 °C

4: 53 percent / Tf₂O / CH₂Cl₂ / -78 - -20 °C

5: H₂O; AcOH / 50 °C

6: pyridine

7: NaN₃ / dimethylformamide

8: PMe₃ / tetrahydrofuran; ethanol; H₂O

9: HATU; DIPEA / dimethylformamide

With pyridine; dmap; formic acid; sodium azide; trifluoromethylsulfonic anhydride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; trimethylphosphane; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Alkylation / 2: Alkylation / 3: detritylation / 4: Substitution / 5: Hydrolysis / 6: Tosylation / 7: Substitution / 8: Reduction / 9: Acetylation;

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

upstream raw materials:

acetic acid

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

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

5'-O-trityluridine

Downstream raw materials:

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