N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide

Base Information

Chemical Name:N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide
CAS No.:140428-40-6
Molecular Formula:C₂₅H₂₉NO₆
Molecular Weight:439.508
Hs Code.:

Synonyms:N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide

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Chemical Property of N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide

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Technology Process of N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide

There total 14 articles about N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide 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: 85.0%

: 140428-39-3
Trifluoro-methanesulfonic acid (3aS,4S,6R,7S,7aR)-4-benzyloxy-6-(2-benzyloxycarbamoyl-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

: 140428-40-6
N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide

Guidance literature:: With potassium carbonate; In acetone; for 1h; Heating;
DOI:10.1246/bcsj.65.567

Reference yield:

: 15548-45-5
(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

: 140428-40-6
N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide

Guidance literature:: Multi-step reaction with 13 steps

1: 75 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 94.3 percent / 2-naphthalenesulfonic acid / acetone / 8 h / Ambient temperature

3: 94 percent / triethylamine / tetrahydrofuran / Ambient temperature

4: 1.) Na / 1.) toluene, reflux, 2.) toluene, reflux, overnight

5: 70 percent / DMSO, NaCl / H₂O / 15 h / 145 °C

6: 1 g / 1 M aq. KOH / methanol / Ambient temperature

7: 96 percent / diethyl ether

8: 95 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / Ambient temperature

9: 97 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

10: 95 percent / 1 M NaOH / ethanol / 15 h / Ambient temperature

11: 85 percent / DCC / tetrahydrofuran / 20 h / Ambient temperature

12: 85 percent / pyridine / CH₂Cl₂ / 15 h / -20 °C

13: 85 percent / K₂CO₃ / acetone / 1 h / Heating

With pyridine; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; naphthalene-2-sulfonate; sodium; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; sodium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone;
DOI:10.1246/bcsj.65.567

Reference yield:

: 117371-06-9
benzyl 6-O-p-toluenesulfonyl-α-D-mannopyranoside

: 140428-40-6
N-Benzyloxy-3-((3aS,4S,7aS)-4-benzyloxy-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-propionamide

Guidance literature:: Multi-step reaction with 12 steps

1: 94.3 percent / 2-naphthalenesulfonic acid / acetone / 8 h / Ambient temperature

2: 94 percent / triethylamine / tetrahydrofuran / Ambient temperature

3: 1.) Na / 1.) toluene, reflux, 2.) toluene, reflux, overnight

4: 70 percent / DMSO, NaCl / H₂O / 15 h / 145 °C

5: 1 g / 1 M aq. KOH / methanol / Ambient temperature

6: 96 percent / diethyl ether

7: 95 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / Ambient temperature

8: 97 percent / NaBH₄ / ethanol / 0.5 h / Ambient temperature

9: 95 percent / 1 M NaOH / ethanol / 15 h / Ambient temperature

10: 85 percent / DCC / tetrahydrofuran / 20 h / Ambient temperature

11: 85 percent / pyridine / CH₂Cl₂ / 15 h / -20 °C

12: 85 percent / K₂CO₃ / acetone / 1 h / Heating

With pyridine; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; naphthalene-2-sulfonate; sodium; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; sodium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone;
DOI:10.1246/bcsj.65.567