hexyl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

Base Information

• Chemical Name: hexyl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide
• CAS No.: 870529-26-3
• Molecular Formula: C₂₉H₄₅N₃O₁₀
• Molecular Weight: 595.69

Synonyms:hexyl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

Chemical Property of hexyl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of hexyl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

There total 10 articles about hexyl 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: 87.0%

[((2S,3S,4R,5R,6R)-5-Amino-6-hexyloxy-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester (870529-39-8) + Boc-D-Phe-OH (18942-49-9) → hexyl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide (870529-26-3)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; at 20 ℃;

DOI:10.1002/hlca.200590175

Reference yield:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) → hexyl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide (870529-26-3)

Guidance literature:

Multi-step reaction with 6 steps

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

1.2: 60.4 percent / TMSOTf / CH₂Cl₂ / 0.5 h

2.1: 85 percent / Na / methanol / 20 °C

3.1: 98 percent / TEMPO; NaClO₂; NaHCO₃ / Borax / acetonitrile; H₂O / 0.5 h / pH 9.0

4.1: 86 percent / HOBt; EDC hydrochloride; Et(iPr)2N / CH₂Cl₂ / 20 °C

5.1: H₂ / Pd/C / ethanol / 760 Torr

6.1: 87 percent / EEDQ / CH₂Cl₂ / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; calcium sulfate; sodium chlorite; hydrogen; sodium; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; borax; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1002/hlca.200590175

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose (114297-26-6) → hexyl 2-{[N-(tert-butoxycarbonyl)-D-phenylalanyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide (870529-26-3)

Guidance literature:

Multi-step reaction with 8 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: 60.4 percent / TMSOTf / CH₂Cl₂ / 0.5 h

4.1: 85 percent / Na / methanol / 20 °C

5.1: 98 percent / TEMPO; NaClO₂; NaHCO₃ / Borax / acetonitrile; H₂O / 0.5 h / pH 9.0

6.1: 86 percent / HOBt; EDC hydrochloride; Et(iPr)2N / CH₂Cl₂ / 20 °C

7.1: H₂ / Pd/C / ethanol / 760 Torr

8.1: 87 percent / EEDQ / CH₂Cl₂ / 20 °C

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; calcium sulfate; sodium chlorite; hydrogen; sodium; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; borax; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; water; acetone; acetonitrile;

DOI:10.1002/hlca.200590175

upstream raw materials:

[((2S,3S,4R,5R,6R)-5-Amino-6-hexyloxy-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester

Boc-D-Phe-OH

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

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

Downstream raw materials:

{[(2S,3S,4R,5R,6R)-5-((R)-2-Amino-3-phenyl-propionylamino)-6-hexyloxy-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-acetic acid methyl ester

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