(tert-butyl)dimethylsilyl 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-glucopyranoside

Base Information

• Chemical Name: (tert-butyl)dimethylsilyl 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-glucopyranoside
• CAS No.: 768387-83-3
• Molecular Formula: C₅₈H₆₈N₂O₁₇Si₂
• Molecular Weight: 1121.35
• Mol file: 768387-83-3.mol

Synonyms:(tert-butyl)dimethylsilyl 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-glucopyranoside

Chemical Property of (tert-butyl)dimethylsilyl 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-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (tert-butyl)dimethylsilyl 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-glucopyranoside

There total 6 articles about (tert-butyl)dimethylsilyl 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-glucopyranoside 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: 96.0%

acetic anhydride (108-24-7) + (tert-butyl)dimethylsilyl 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-glucopyranoside (768387-75-3) → (tert-butyl)dimethylsilyl 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-glucopyranoside (768387-83-3)

Guidance literature:

With pyridine; at 20 ℃;

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) → (tert-butyl)dimethylsilyl 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-glucopyranoside (768387-83-3)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; sodium methylate; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200490160

Reference yield:

(tert-butyl)dimethylsilyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (732246-93-4) → (tert-butyl)dimethylsilyl 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-glucopyranoside (768387-83-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 64 percent / 4 Angstroem MS; Me₃SiOTf / diethyl ether / 0.5 h / 0 °C

3: 96 percent / pyridine / 20 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/hlca.200490160

upstream raw materials:

acetic anhydride

(tert-butyl)dimethylsilyl 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-glucopyranoside

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₅₄H₆₆Cl₆N₂O₂₂Si

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

O-3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->4)-O-3-O-acetyl-2-(acetylamino)-6-O-[(tert-butyl)diphenylsilyl]-2-deoxy-β-D-glucopyranosyl-(1->2)-1,4-di-O-acetyl-3-O-(aminocarbonyl)-α-D-glucopyranuronamide

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