1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil

Base Information

• Chemical Name: 1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil
• CAS No.: 1453217-80-5
• Molecular Formula: C₄₄H₄₈N₂O₉Si
• Molecular Weight: 776.959
• Mol file: 1453217-80-5.mol

Synonyms:1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil

Chemical Property of 1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil

There total 6 articles about 1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil 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: 91.0%

C42H48O9Si (1453217-81-6) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil (1453217-80-5)

Guidance literature:

uracil; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 90 ℃; for 1h; Inert atmosphere;

C₄₂H₄₈O₉Si; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 50 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jo401170y

Reference yield:

((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (956485-08-8) → 1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil (1453217-80-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridinium chlorochromate / dichloromethane / 13 h / 40 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -41 °C / Inert atmosphere

2.2: 2 h / -41 °C / Inert atmosphere

3.1: pyridine / 24 h / 110 °C / Inert atmosphere

4.1: acetic acid; water / 3 h / 90 °C

5.1: pyridine / 12 h / 23 °C / Inert atmosphere

6.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 90 °C / Inert atmosphere

6.2: 16 h / 0 - 50 °C / Inert atmosphere

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; boron trifluoride diethyl etherate; water; acetic acid; pyridinium chlorochromate; In dichloromethane; acetonitrile; 2.1: |Sakurai Allylation / 6.1: |Vorbrueggen Nucleoside Synthesis / 6.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/jo401170y

Reference yield:

(3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde → 1-(2,5-O-diacetyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil (1453217-80-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -41 °C / Inert atmosphere

1.2: 2 h / -41 °C / Inert atmosphere

2.1: pyridine / 24 h / 110 °C / Inert atmosphere

3.1: acetic acid; water / 3 h / 90 °C

4.1: pyridine / 12 h / 23 °C / Inert atmosphere

5.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 90 °C / Inert atmosphere

5.2: 16 h / 0 - 50 °C / Inert atmosphere

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; boron trifluoride diethyl etherate; water; acetic acid; In dichloromethane; acetonitrile; 1.1: |Sakurai Allylation / 5.1: |Vorbrueggen Nucleoside Synthesis / 5.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/jo401170y

upstream raw materials:

((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

(S)-1-((3aR,5S,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-ol

1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-acetyl-6-deoxy-6-C-vinyl-β-L-mannofuranose

C₄₂H₄₈O₉Si

Downstream raw materials:

C₄₂H₄₆N₂O₈Si

1-(2-O-methanesulfonyl-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-acetyl-6-deoxy-6-C-vinyl-α-L-mannofuranosyl)uracil

C₄₂H₄₄N₂O₇Si