1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside

Base Information

• Chemical Name: 1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside
• CAS No.: 166191-09-9
• Molecular Formula: C₂₁H₂₉F₃N₂O₇Si
• Molecular Weight: 506.551
• Mol file: 166191-09-9.mol

Synonyms:1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside

Chemical Property of 1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside

There total 2 articles about 1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside 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:

3-azido-1-O-tert-butyl(dimethyl)silyl-2,3,6-trideoxy-β-L-arabino-hexopyranose (128135-57-9) → 1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside (166191-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / triethylamine; hydrogen / 10 percent Pd-C / methanol / 4 h

2: 91 percent / 4-dimethylaminopyridine; pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; dmap; hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)00257-3

Reference yield:

Acetic acid (2S,3R,6R)-4-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-3-yl ester (203571-04-4) → 1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside (166191-09-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / K₂CO₃ / methanol / 15 h

2: 82 percent / triethylamine; hydrogen / 10 percent Pd-C / methanol / 4 h

3: 91 percent / 4-dimethylaminopyridine; pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; dmap; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(00)00257-3

Reference yield: 70.0%

ε-iso-rhodomycinone (21204-32-0) + 1-O-tert-butyldimethylsilyl 4-O-p-nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside (166191-09-9) → 7-O-(4-O-p-Nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-α-L-arabino-hexopyranosyl)-ε-isorhodomycinone (130320-86-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; acetone; at -35 ℃; for 6h;

DOI:10.1016/S0008-6215(00)00257-3

upstream raw materials:

Acetic acid (2S,3R,6R)-4-azido-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-3-yl ester

3-azido-1-O-tert-butyl(dimethyl)silyl-2,3,6-trideoxy-β-L-arabino-hexopyranose

Downstream raw materials:

7-O-(4-O-p-Nitrobenzoyl-2,3,6-trideoxy-3-trifluoroacetylamido-α-L-arabino-hexopyranosyl)-ε-isorhodomycinone