Acetic acid (2R,4aR,6R,7S,8S,8aR)-7-acetoxy-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

Chemical Name:Acetic acid (2R,4aR,6R,7S,8S,8aR)-7-acetoxy-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
CAS No.:89992-76-7
Molecular Formula:C₂₇H₃₈O₈
Molecular Weight:490.594
Hs Code.:

Acetic acid (2R,4aR,6R,7S,8S,8aR)-7-acetoxy-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Chemical Property of Acetic acid (2R,4aR,6R,7S,8S,8aR)-7-acetoxy-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Technology Process of Acetic acid (2R,4aR,6R,7S,8S,8aR)-7-acetoxy-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 22 articles about Acetic acid (2R,4aR,6R,7S,8S,8aR)-7-acetoxy-6-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 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:

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

: 89992-76-7,115648-29-8
(-)-menthyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 8 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

7: 82 percent / pyridine / dimethylformamide / 2 h / 70 °C

8: 1.) 0.1 percent sodium methoxide, methanol, 2.) 4-dimethylaminopyridine, pyridine / 1.) dichloromethane, r.t., 10 min 2.) dichloromethane, overnight

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

Reference yield:

: 115533-28-3
3-O-(N-phenylcarbamoyl)-D-glucopyranose

: 89992-76-7,115648-29-8
(-)-menthyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

2: 40 percent / trimethylsilyl triflate / CH₂Cl₂ / 144 h / Ambient temperature

3: K₂CO₃ / methanol / 5.5 h / Ambient temperature

4: 54 percent HBF₄ / dimethylformamide; diethyl ether / 2 h / Ambient temperature

5: 87 percent / pyridine / CH₂Cl₂ / 0.75 h / -15 °C

6: 82 percent / pyridine / dimethylformamide / 2 h / 70 °C

7: 1.) 0.1 percent sodium methoxide, methanol, 2.) 4-dimethylaminopyridine, pyridine / 1.) dichloromethane, r.t., 10 min 2.) dichloromethane, overnight

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

Reference yield:

: 34368-65-5
1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose

: 89992-76-7,115648-29-8
(-)-menthyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: aq. acetic acid

2: 87 percent / 0.05 M H₂SO₄ / dioxane / 5 h / 100 °C

3: 93 percent / pyridine, 4-dimethylaminopyridine / 5 h / Ambient temperature

4: 40 percent / trimethylsilyl triflate / CH₂Cl₂ / 144 h / Ambient temperature

5: K₂CO₃ / methanol / 5.5 h / Ambient temperature

6: 54 percent HBF₄ / dimethylformamide; diethyl ether / 2 h / Ambient temperature

7: 87 percent / pyridine / CH₂Cl₂ / 0.75 h / -15 °C

8: 82 percent / pyridine / dimethylformamide / 2 h / 70 °C

9: 1.) 0.1 percent sodium methoxide, methanol, 2.) 4-dimethylaminopyridine, pyridine / 1.) dichloromethane, r.t., 10 min 2.) dichloromethane, overnight

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