Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside

Base Information

• Chemical Name: Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside
• CAS No.: 116663-02-6
• Molecular Formula: C₁₆H₁₈F₃NO₅
• Molecular Weight: 361.318

Synonyms:Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside

Chemical Property of Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside

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Technology Process of Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside

There total 2 articles about Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-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: 100.0%

Methyl 3-amino-4,6-O-benzylidene-2,3-dideoxy-β-D-ribo-hexopyranoside (116663-00-4) + trifluoroacetic anhydride (407-25-0) → Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside (116663-02-6)

Guidance literature:

With pyridine; In diethyl ether; at 0 ℃; for 3h;

DOI:10.1016/0008-6215(88)84145-4

Reference yield:

(2R,4aR,6R,8S,8aS)-8-Azido-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine → Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside (116663-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂ / Pd/CaCO₃ 5percent / methanol / 4 h

2: 100 percent / pyridine / diethyl ether / 3 h / 0 °C

With pyridine; hydrogen; Lindlar's catalyst; In methanol; diethyl ether;

DOI:10.1016/0008-6215(88)84145-4

Reference yield: 90.0%

Methyl 4,6-O-benzylidene-2,3-dideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside (116663-02-6) → Methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside (116594-44-6)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 4h; Heating;

DOI:10.1016/0008-6215(88)84145-4

upstream raw materials:

Methyl 3-amino-4,6-O-benzylidene-2,3-dideoxy-β-D-ribo-hexopyranoside

trifluoroacetic anhydride

Downstream raw materials:

Methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-3-trifluoroacetamido-β-D-ribo-hexopyranoside

(2S,3S,5S)-2-benzoyloxy-5-hydroxy-3-trifluoroacetamidocyclohexanone

Methyl 4-O-benzoyl-2,3,6-trideoxy-3-trifluoroacetamido-β-D-erythro-hex-5-enopyranoside

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