methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside

Base Information

• Chemical Name: methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside
• CAS No.: 73366-86-6
• Molecular Formula: C₉H₁₄F₃NO₄
• Molecular Weight: 257.21
• Mol file: 73366-86-6.mol

Synonyms:methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside

Chemical Property of methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside

There total 1 articles about methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-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:

acetic anhydride (108-24-7) + methyl 2,3,6-trideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside (77068-14-5) → acetyl-di-O-acetyl-3,4 didesoxy-2,6 L-lyxo-hexopyrannose (33985-28-3) + methyl 4-O-acetyl-2,3,6-tridesoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside (75412-33-8) + methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside (73366-86-6) + (2S,4S,5R,6S)-6-methyl-tetrahydro-2H-pyran-2,4,5-triyl triacetate (33985-27-2)

Guidance literature:

With pyridine; acetic acid; Yield given. Multistep reaction; 2.) 16h, CH₂Cl₂;

DOI:10.1016/0040-4020(81)85015-6

Reference yield: 89.0%

methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside (73366-86-6) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside (81703-97-1)

Guidance literature:

With toluene-4-sulfonic acid; In hexane; Heating;

DOI:10.1039/c39830000305

Reference yield:

methyl 2,3,6-trideoxy-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside (73366-86-6) → N-{(2S,3S,4S,6R)-6-Benzyloxy-3-[(2S,4S,5R,6S)-4-benzyloxy-6-methyl-5-((2R,6S)-6-methyl-5-oxo-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-methyl-tetrahydro-pyran-4-yl}-2,2,2-trifluoro-acetamide

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / p-Me-C₆H₄-SO₃H / hexane / Heating

2: 1.) bromotrimethylsilane, 2.) HgBr₂, HgO / 1.) benzene, r.t., 2.) CH₂Cl₂, 15 min 0 deg C then 1 h r.t.

3: NaOMe / methanol

4: 68 percent / N-iodosuccinimide / acetonitrile / 1 h / 0 °C

5: H₂, Et₃N / Pd-C / ethanol

7: 90 percent / pyridinium dichromate / CH₂Cl₂

With N-iodo-succinimide; dipyridinium dichromate; trimethylsilyl bromide; hydrogen; sodium methylate; toluene-4-sulfonic acid; triethylamine; mercury dibromide; mercury(II) oxide; palladium on activated charcoal; In methanol; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1039/c39830000305

upstream raw materials:

acetic anhydride

methyl 2,3,6-trideoxy-4-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-3-(trifluoroacetamido)-β-L-lyxo-hexopyranoside

Downstream raw materials:

benzyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

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

benzyl 4-O-(3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside

benzyl 4-O-(4-O-acetyl-3-O-benzyl-2,6-dideoxy-α-L-lyxo-hexopyranosyl)-2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexopyranoside