(3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

Base Information

Chemical Name:(3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester
CAS No.:357271-78-4
Molecular Formula:C₂₁H₂₉NO₈
Molecular Weight:423.463
Hs Code.:

Synonyms:(3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

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Chemical Property of (3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

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Technology Process of (3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

There total 8 articles about (3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl 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: 77.0%

: 357271-77-3
(3aR,4R,6R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

: 74-88-4
methyl iodide

: 357271-78-4
(3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -70 ℃; for 0.583333h;
DOI:10.1021/ol010119s

Reference yield:

: (3aR,4R,6S,7S,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

: 357271-78-4
(3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 98.7 percent / Et₃N / 168 h / 23 °C

2: 85 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 0.266 g / KH; 18-crown-6 / tetrahydrofuran / 4 h / -30 °C

4: NaOH / H₂O / 4 h / Heating

5: 542 mg / K₂CO₃ / dioxane; H₂O / 10 h / 23 °C

6: 93.1 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -61 - 0 °C

7: 84 percent / I₂; KOH / 0.75 h / 0 °C

8: 77 percent / KN(SiMe₃)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.58 h / -70 °C

With pyridine; potassium hydroxide; sodium hydroxide; oxalyl dichloride; 18-crown-6 ether; iodine; potassium hydride; potassium hexamethylsilazane; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;
DOI:10.1021/ol010119s

Reference yield:

: 357271-85-3
((3aR,4R,6R,7R,7aR)-4-Methoxy-2,2-dimethyl-7-methylamino-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

: 357271-78-4
(3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 542 mg / K₂CO₃ / dioxane; H₂O / 10 h / 23 °C

2: 93.1 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -61 - 0 °C

3: 84 percent / I₂; KOH / 0.75 h / 0 °C

4: 77 percent / KN(SiMe₃)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.58 h / -70 °C

With potassium hydroxide; oxalyl dichloride; iodine; potassium hexamethylsilazane; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;
DOI:10.1021/ol010119s