(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester
CAS No.:726192-33-2
Molecular Formula:C₂₆H₃₈N₂O₈
Molecular Weight:506.596
Hs Code.:

(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Synonyms:(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

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Chemical Property of (3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

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Technology Process of (3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

There total 7 articles about (3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl 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: 74.0%

: 16652-76-9
L-valine benzyl ester p-toluenesulfonate salt

: 726192-17-2
D-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyproline

: 726192-33-2
(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 1h;
DOI:10.1021/jo049637h

Reference yield:

: 573716-70-8
(-)-(1S,2R,3S,4R,5S,6R)-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane-5-endo-ol

: 726192-33-2
(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / Na/Hg / methanol; tetrahydrofuran / 0.5 h / -15 °C

2.1: 91 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -70 - 20 °C

3.1: 86 percent / Et₃N / dimethylformamide / 6 h / 60 °C

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

4.2: 88 percent / NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

5.1: 74 percent / PyAOP; diisopropylethylamine / dimethylformamide / 1 h

With sodium amalgam; oxalyl dichloride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2.1: Swern oxidation;
DOI:10.1021/jo049637h

Reference yield:

: 726192-16-1
(3aS,4R,7R,7aR)-tert-butyl 2,2-dimethyl-5-oxohexahydro-4,7-epiminobenzo[d][1,3]dioxole-8-carboxylate

: 726192-33-2
(3aS,4R,6R,6aR)-4-((S)-1-Benzyloxycarbonyl-2-methyl-propylcarbamoyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / Et₃N / dimethylformamide / 6 h / 60 °C

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

2.2: 88 percent / NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

3.1: 74 percent / PyAOP; diisopropylethylamine / dimethylformamide / 1 h

With ozone; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049637h