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

Base Information

• Chemical Name: 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
• CAS No.: 264128-16-7
• Molecular Formula: C₇₄H₉₈N₄O₁₅
• Molecular Weight: 1283.61
• Mol file: 264128-16-7.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 16 articles about 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 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) → 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 (264128-16-7)

Guidance literature:

Multi-step reaction with 12 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 / 12: Addition;

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

Reference yield:

5'-O-trityluridine (6554-10-5) → 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 (264128-16-7)

Guidance literature:

Multi-step reaction with 9 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 / 9: Addition;

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

Reference yield:

uridine (58-96-8) → 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 (264128-16-7)

Guidance literature:

Multi-step reaction with 10 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 / 10: Addition;

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

upstream raw materials:

octadecyl isocyanate

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

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

5'-O-trityluridine