methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside

Base Information

• Chemical Name: methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside
• CAS No.: 81090-82-6
• Molecular Formula: C₁₆H₁₇BrF₃NO₅
• Molecular Weight: 440.214
• Mol file: 81090-82-6.mol

Synonyms:methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside

Chemical Property of methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside

There total 6 articles about methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-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: 88.0%

methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside → methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside (81090-82-6)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 1.5h; Irradiation;

DOI:10.1246/bcsj.59.663

Reference yield:

(4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one oxime → methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside (81090-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaAlH₂(OCH₂CH₂OMe)2C₆H₅Me, NaOH / 1.) toluene, -40 deg C, 0.5 h; 2.) H₂O; 3.) pyridine, 0 deg C, 3 h

2: 88 percent / N-bromosuccinimide, BaCO₃ / CCl₄ / 1.5 h / Irradiation

With sodium hydroxide; N-Bromosuccinimide; sodium bis(2-methoxyethoxy)aluminium dihydride; barium carbonate; In tetrachloromethane;

DOI:10.1246/bcsj.59.663

Reference yield:

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose (63598-31-2) → methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside (81090-82-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / NH₂OH*HCl, NaOH / ethanol / 24 h / Ambient temperature

2: 66 percent / LiAlH₄ / diethyl ether / 20 h / Heating

3: Et₃N / CCl₄ / 0.5 h

4: BaCO₃, NBS / CCl₄ / 3 h / Heating

With sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; triethylamine; barium carbonate; In tetrachloromethane; diethyl ether; ethanol;

upstream raw materials:

methyl 4,6-O-benzylidene-3-trifluoroacetamido-2,3-dideoxy-α-D-ribo-hexopyranoside

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranosid-3-ulose oxime

methyl 3-amino-4,6-O-benzylidene-2,3-dideoxy-α-D-ribo-hexopyranoside

Downstream raw materials:

methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside

Benzoic acid (2S,3S,4S,6S)-2-iodomethyl-6-methoxy-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

2,3,6-Trideoxy-3-trifluoroacetamido-L-lixo-hexopyranose

Benzoic acid (2R,3S,4S,6S)-6-methoxy-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester