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

Base Information

• Chemical Name: methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside
• CAS No.: 81090-83-7
• Molecular Formula: C₁₆H₁₆F₃NO₅
• Molecular Weight: 359.302
• Mol file: 81090-83-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside 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: 90.0%

methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside (81090-82-6) → methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside (81090-83-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N,N,N,N,N-hexamethylphosphoric triamide; Ambient temperature;

Reference yield:

(4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one oxime → methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside (81090-83-7)

Guidance literature:

Multi-step reaction with 3 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

3: 75 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 2.5 h / Heating

With sodium hydroxide; N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium bis(2-methoxyethoxy)aluminium dihydride; barium carbonate; In tetrachloromethane; benzene;

DOI:10.1246/bcsj.59.663

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-α-D-ribo-hexopyranoside → methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-α-D-erythro-hex-5-enopyranoside (81090-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / N-bromosuccinimide, BaCO₃ / CCl₄ / 1.5 h / Irradiation

2: 75 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 2.5 h / Heating

With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; barium carbonate; In tetrachloromethane; benzene;

DOI:10.1246/bcsj.59.663

upstream raw materials:

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

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

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

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

Downstream raw materials:

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