(-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside

Base Information

Chemical Name:(-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside
CAS No.:115533-45-4
Molecular Formula:C₃₁H₃₈F₃NO₉S
Molecular Weight:657.705
Hs Code.:

Synonyms:(-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside

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Chemical Property of (-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside

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Technology Process of (-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside

There total 20 articles about (-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside 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: 87.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 115533-41-0,142184-42-7
(-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-β-D-glucopyranoside

: 115533-45-4
(-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside

Guidance literature:: With pyridine; In dichloromethane; at -15 ℃; for 0.75h;
DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

: 34368-66-6
1,2-O-isopropylidene-3-O-phenylcarbamoyl-α-D-glucofuranose

: 115533-45-4
(-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / 0.05 M H₂SO₄ / dioxane / 5 h / 100 °C

2: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

3: 40 percent / trimethylsilyl triflate / CH₂Cl₂ / 144 h / Ambient temperature

4: K₂CO₃ / methanol / 5.5 h / Ambient temperature

5: 54 percent HBF₄ / dimethylformamide; diethyl ether / 2 h / Ambient temperature

6: 87 percent / pyridine / CH₂Cl₂ / 0.75 h / -15 °C

With pyridine; dmap; tetrafluoroboric acid; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; potassium carbonate; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90561-5

Reference yield:

: 103-71-9
phenyl isocyanate

: 115533-45-4
(-)-menthyl 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-2-O-trifluoromethanesulfonyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / 4-dimethylaminopyridine / toluene / 3 h / 100 °C

2: aq. acetic acid

3: 87 percent / 0.05 M H₂SO₄ / dioxane / 5 h / 100 °C

4: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

5: 40 percent / trimethylsilyl triflate / CH₂Cl₂ / 144 h / Ambient temperature

6: K₂CO₃ / methanol / 5.5 h / Ambient temperature

7: 54 percent HBF₄ / dimethylformamide; diethyl ether / 2 h / Ambient temperature

8: 87 percent / pyridine / CH₂Cl₂ / 0.75 h / -15 °C

With pyridine; dmap; tetrafluoroboric acid; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; potassium carbonate; acetic acid; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0008-6215(00)90561-5