(S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

Base Information

• Chemical Name: (S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester
• CAS No.: 155023-02-2
• Molecular Formula: C₂₃H₂₉N₃O₉
• Molecular Weight: 491.498
• Mol file: 155023-02-2.mol

Synonyms:(S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

Chemical Property of (S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester

There total 15 articles about (S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl 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:

(R)-Hydroxy-((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester (58056-16-9,64697-70-7,64697-71-8,123155-56-6) → (S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester (155023-02-2)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / CH₂Cl₂ / 0 °C

2: NaN₃ / dimethylformamide / Ambient temperature

3: Dowex 50w X₈, MeOH / Ambient temperature

4: 1.) pyridine, 2.) H₂SO₄, AcOH / 2.) CH₂Cl₂

5: 93 percent / Me₃SiOSO₂CF₃ / CH₂Cl₂ / Ambient temperature

6: H₂ / 5percent Pd/BaSO₄ / dioxane; H₂O

7: aq. Ba(OH)2 / dioxane / Ambient temperature

8: aq. K₂CO₃ / dioxane

9: NaHCO₃ / dimethylformamide / Ambient temperature

With pyridine; methanol; barium dihydroxide; sodium azide; trimethylsilyl trifluoromethanesulfonate; Dowex 50W X₈; sulfuric acid; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; Pd-BaSO₄; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c39940000111

Reference yield:

(R)-((2S,3S,4R,5S)-3,4-Dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-hydroxy-acetic acid methyl ester (10357-01-4,10357-02-5,18486-26-5,18486-29-8,18486-45-8,18486-46-9,58056-17-0,135414-73-2,135414-76-5) → (S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester (155023-02-2)

Guidance literature:

Multi-step reaction with 10 steps

1: TsOH / dimethylformamide / Ambient temperature

2: pyridine / CH₂Cl₂ / 0 °C

3: NaN₃ / dimethylformamide / Ambient temperature

4: Dowex 50w X₈, MeOH / Ambient temperature

5: 1.) pyridine, 2.) H₂SO₄, AcOH / 2.) CH₂Cl₂

6: 93 percent / Me₃SiOSO₂CF₃ / CH₂Cl₂ / Ambient temperature

7: H₂ / 5percent Pd/BaSO₄ / dioxane; H₂O

8: aq. Ba(OH)2 / dioxane / Ambient temperature

9: aq. K₂CO₃ / dioxane

10: NaHCO₃ / dimethylformamide / Ambient temperature

With pyridine; methanol; barium dihydroxide; sodium azide; trimethylsilyl trifluoromethanesulfonate; Dowex 50W X₈; sulfuric acid; hydrogen; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; Pd-BaSO₄; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c39940000111

Reference yield:

methyl (5-azido-5-deoxy-1,2,3-tri-O-acetyl-D-allofuranosid)uronate (155154-68-0) → (S)-tert-Butoxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid benzyl ester (155023-02-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / Me₃SiOSO₂CF₃ / CH₂Cl₂ / Ambient temperature

2: H₂ / 5percent Pd/BaSO₄ / dioxane; H₂O

3: aq. Ba(OH)2 / dioxane / Ambient temperature

4: aq. K₂CO₃ / dioxane

5: NaHCO₃ / dimethylformamide / Ambient temperature

With barium dihydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; potassium carbonate; Pd-BaSO₄; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c39940000111

upstream raw materials:

benzyl bromide

(R)-Hydroxy-((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester

(R)-((2S,3S,4R,5S)-3,4-Dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-hydroxy-acetic acid methyl ester

Methyl 5-amino-1,5-dideoxy-1-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronate 2,3-diacetate