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

Base Information

• Chemical Name: hexyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide
• CAS No.: 870529-18-3
• Molecular Formula: C₂₃H₃₄N₂O₉
• Molecular Weight: 482.531

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

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

Chemical Property:

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

There total 9 articles about hexyl 2-{[(benzyloxy)carbonyl]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: 86.0%

hexyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid (870529-11-6) + glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) → hexyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide (870529-18-3)

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:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) → hexyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide (870529-18-3)

Guidance literature:

Multi-step reaction with 4 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

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; calcium sulfate; sodium chlorite; sodium; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; borax; In methanol; 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-{[(benzyloxy)carbonyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide (870529-18-3)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1002/hlca.200590175

upstream raw materials:

hexyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid

glycine ethyl ester hydrochloride

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

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

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