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

Base Information

• Chemical Name: 1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-acetyl-6-deoxy-6-C-vinyl-β-L-mannofuranose
• CAS No.: 1453217-79-2
• Molecular Formula: C₄₁H₄₈O₇Si
• Molecular Weight: 680.913
• Mol file: 1453217-79-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-acetyl-6-deoxy-6-C-vinyl-β-L-mannofuranose 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: 84.0%

(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 (1453217-78-1) + acetic anhydride (108-24-7) → 1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-acetyl-6-deoxy-6-C-vinyl-β-L-mannofuranose (1453217-79-2)

Guidance literature:

With pyridine; at 110 ℃; for 24h; 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-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-acetyl-6-deoxy-6-C-vinyl-β-L-mannofuranose (1453217-79-2)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; boron trifluoride diethyl etherate; pyridinium chlorochromate; In dichloromethane; 2.1: |Sakurai Allylation;

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-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-acetyl-6-deoxy-6-C-vinyl-β-L-mannofuranose (1453217-79-2)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; boron trifluoride diethyl etherate; In dichloromethane; 1.1: |Sakurai Allylation;

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

acetic anhydride

Downstream raw materials:

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

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