prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Base Information

• Chemical Name: prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone
• CAS No.: 768387-78-6
• Molecular Formula: C₆₄H₆₈N₂O₂₂Si
• Molecular Weight: 1245.33
• Mol file: 768387-78-6.mol

Synonyms:prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Chemical Property of prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

There total 10 articles about prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone 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: 42.0%

prop-2-enyl 5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone (768387-90-2) + 3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranosyl trichloroacetimidate (768387-85-5) → prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone (768387-78-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1002/hlca.200490160

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3) → prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone (768387-78-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / 1H-imidazole / dimethylformamide / 4 h / 20 °C

2: 95 percent / NaOMe / methanol / 4 h / 20 °C

3: 88 percent / 1H-imidazole / dimethylformamide / 2 h / 0 °C

4: 64 percent / 4 Angstroem MS; Me₃SiOTf / diethyl ether / 0.5 h / 0 °C

5: 96 percent / pyridine / 20 °C

6: 78 percent / Bu₄NF / tetrahydrofuran / 0.08 h / -20 °C

7: 86 percent / K₂CO₃ / CH₂Cl₂ / 20 °C

8: 42 percent / 4 Angstroem MS; Me₃SiOTf / diethyl ether / 0.5 h / 0 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; tetrabutyl ammonium fluoride; sodium methylate; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200490160

Reference yield:

1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosidurono-6,3-lactone (126214-82-2) → prop-2-enyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->4)-O-[3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-β-D-glucopyranosyl]-(1->2)-5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone (768387-78-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / TFA / H₂O / 0.67 h / 20 °C

2: 49 percent / camphorsulfonic acid / 2.5 h / 20 °C

3: 42 percent / 4 Angstroem MS; Me₃SiOTf / diethyl ether / 0.5 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; camphor-10-sulfonic acid; trifluoroacetic acid; In diethyl ether; water;

DOI:10.1002/hlca.200490160

upstream raw materials:

prop-2-enyl 5-O-prop-2-enyl-β-D-glucofuranosidurono-6,3-lactone

3-O-acetyl-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-2-phthalimido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranosyl trichloroacetimidate

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

1,2-O-isopropyliden-5-O-allyl-α-D-glucofuranosidurono-6,3-lactone