methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

Base Information

Chemical Name:methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate
CAS No.:508209-71-0
Molecular Formula:C₃₂H₃₇N₃O₁₂
Molecular Weight:655.659
Hs Code.:

Synonyms:methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

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Chemical Property of methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

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Technology Process of methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

There total 11 articles about methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 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: 54.0%

: 508209-70-9
methyl {3-[5-(3-bromopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

: 508209-71-0
methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 24h;
DOI:10.1002/1099-0690(200212)2002:23<3966::AID-EJOC3966>3.0.CO;2-P

Reference yield:

: 1878-67-7
3-Bromophenylacetic acid

: 508209-71-0
methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / H₂SO₄ / Heating

2: 96 percent / Na₂CO₃ / Pd(PPh₃)4 / toluene; H₂O / 16 h / Heating

3: 60 percent / BBr₃ / CH₂Cl₂ / 10 h / -10 °C

4: BF₃*Et₂O / 1,2-dichloro-ethane / 24 h / 20 °C

5: 93 percent / AlCl₃ / CH₂Cl₂ / 1 h / 0 °C

6: 69 percent / BH₃*THF / 3 h / 20 °C

7: 54 percent / NaN₃ / dimethylformamide / 24 h / 50 °C

With aluminium trichloride; sodium azide; borane-THF; boron tribromide; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; boron trifluoride diethyl etherate; In dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 5: Friedel-Crafts acylation;
DOI:10.1002/1099-0690(200212)2002:23<3966::AID-EJOC3966>3.0.CO;2-P

Reference yield:

: 5720-06-9
2-Methoxyphenylboronic acid

: 508209-71-0
methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / Na₂CO₃ / Pd(PPh₃)4 / toluene; H₂O / 16 h / Heating

2: 60 percent / BBr₃ / CH₂Cl₂ / 10 h / -10 °C

3: BF₃*Et₂O / 1,2-dichloro-ethane / 24 h / 20 °C

4: 93 percent / AlCl₃ / CH₂Cl₂ / 1 h / 0 °C

5: 69 percent / BH₃*THF / 3 h / 20 °C

6: 54 percent / NaN₃ / dimethylformamide / 24 h / 50 °C

With aluminium trichloride; sodium azide; borane-THF; boron tribromide; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; In dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 4: Friedel-Crafts acylation;
DOI:10.1002/1099-0690(200212)2002:23<3966::AID-EJOC3966>3.0.CO;2-P