{[(3aR,4S,6S,6aS)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-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 Name:{[(3aR,4S,6S,6aS)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl]-amino}-acetic acid benzyl ester
CAS No.:726192-24-1
Molecular Formula:C₃₂H₄₁N₃O₉
Molecular Weight:611.692
Hs Code.:

{[(3aR,4S,6S,6aS)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl]-amino}-acetic acid benzyl ester

Synonyms:{[(3aR,4S,6S,6aS)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-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)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-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)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl]-amino}-acetic acid benzyl ester

There total 9 articles about {[(3aR,4S,6S,6aS)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-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: 72.0%

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 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

: 726192-24-1
{[(3aR,4S,6S,6aS)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbonyl]-amino}-acetic acid benzyl ester

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

: 726192-24-1
{[(3aR,4S,6S,6aS)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-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 7 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

7.1: 72 percent / diisopropylethylamine; PyAOP / dimethylformamide / 1 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:

: (+/-)-7-tert-butoxycarbonyl-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one

: 726192-24-1
{[(3aR,4S,6S,6aS)-5-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-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 7 steps

1.1: 44 percent / molecular sieves 4 Angstroem; triethylamine / CH₂Cl₂ / 24 h / 20 °C

2.1: 92 percent / H₃PO₄ / tetrahydrofuran / 0.5 h / 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

7.1: 72 percent / diisopropylethylamine; PyAOP / dimethylformamide / 1 h

With phosphoric acid; 4 A molecular sieve; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo049637h