[((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester

Base Information

Chemical Name:[((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester
CAS No.:726192-23-0
Molecular Formula:C₁₈H₂₄N₂O₆
Molecular Weight:364.398
Hs Code.:

Synonyms:[((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester

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Chemical Property of [((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester

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Technology Process of [((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester

There total 8 articles about [((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl 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: 78.0%

: 726192-32-1
(3aR,4S,6S,6aS)-4-(Benzyloxycarbonylmethyl-carbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

: 726192-23-0
[((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; for 0.5h;
DOI:10.1021/jo049637h

Reference yield:

: 573716-72-0
(+)-(1R,2S,3R,4S,5R,6S)-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane-5-endo-ol

: 726192-23-0
[((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Na/Hg / methanol; tetrahydrofuran / 0.5 h / -15 °C

2.1: 90 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -70 - 20 °C

3.1: 84 percent / Et₃N / dimethylformamide / 6 h / 60 °C

4.1: O₃ / CH₂Cl₂; methanol / 0.42 h / -78 °C

4.2: 89 percent / NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

5.1: 80 percent / PyBOP; diisopropylethylamine / dimethylformamide / 1 h

6.1: 78 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h

With sodium amalgam; oxalyl dichloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Swern oxidation;
DOI:10.1021/jo049637h

Reference yield:

: 726192-15-0
(3aR,4S,7S,7aS)-tert-butyl 2,2-dimethyl-5-oxohexahydro-4,7-epiminobenzo[d][1,3]dioxole-8-carboxylate

: 726192-23-0
[((3aR,4S,6S,6aS)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl)-amino]-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 84 percent / Et₃N / dimethylformamide / 6 h / 60 °C

2.1: O₃ / CH₂Cl₂; methanol / 0.42 h / -78 °C

2.2: 89 percent / NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

3.1: 80 percent / PyBOP; diisopropylethylamine / dimethylformamide / 1 h

4.1: 78 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049637h