1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

Base Information

Chemical Name:1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide
CAS No.:870529-27-4
Molecular Formula:C₃₃H₄₉N₃O₁₀
Molecular Weight:647.766
Hs Code.:

1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

Synonyms:1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

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Chemical Property of 1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

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Technology Process of 1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

There total 9 articles about 1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide 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: 79.8%

: 870529-40-1
{[(2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-((1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxy)-tetrahydro-pyran-2-carbonyl]-amino}-acetic acid methyl ester

: 18942-49-9
Boc-D-Phe-OH

: 870529-27-4
1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;
DOI:10.1002/hlca.200590175

Reference yield:

: 35946-66-8
2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

: 870529-27-4
1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: Drierite; 3A MS / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 58.6 percent / TMSOTf / CH₂Cl₂ / 0.75 h

2.1: Na / methanol / 20 °C

2.2: 53 percent / TEMPO; NaClO₂; NaHCO₃ / Borax / acetonitrile; H₂O / 0.5 h / pH 9.0

3.1: 88 percent / HOBt; EDC hydrochloride; Et(iPr)2N / CH₂Cl₂ / 20 °C

4.1: H₂ / Pd/C / ethanol / 760 Torr

5.1: 79.8 percent / HOBt; EDC hydrochloride; Et(iPr)2)N / CH₂Cl₂ / 20 °C

With calcium sulfate; hydrogen; sodium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane;
DOI:10.1002/hlca.200590175

Reference yield:

: 114297-26-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose

: 870529-27-4
1,3,3-trimethylbicyclo[2.2.1]hept-2-yl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / HCl / acetone

2.1: 83 percent / NaHCO₃ / CHCl₃; H₂O / pH 8.0

3.1: Drierite; 3A MS / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 58.6 percent / TMSOTf / CH₂Cl₂ / 0.75 h

4.1: Na / methanol / 20 °C

4.2: 53 percent / TEMPO; NaClO₂; NaHCO₃ / Borax / acetonitrile; H₂O / 0.5 h / pH 9.0

5.1: 88 percent / HOBt; EDC hydrochloride; Et(iPr)2N / CH₂Cl₂ / 20 °C

6.1: H₂ / Pd/C / ethanol / 760 Torr

7.1: 79.8 percent / HOBt; EDC hydrochloride; Et(iPr)2)N / CH₂Cl₂ / 20 °C

With hydrogenchloride; calcium sulfate; hydrogen; sodium; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; water; acetone;
DOI:10.1002/hlca.200590175