2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid

Base Information

• Chemical Name: 2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid
• CAS No.: 322407-76-1
• Molecular Formula: C₁₇H₂₅N₃O₉
• Molecular Weight: 415.4

Synonyms:2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid

Chemical Property of 2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid

Chemical Property:

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Technology Process of 2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid

There total 1 articles about 2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid 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: 63.0%

2-(2,4,5,8-tetrahydroxy-7-oxa-2-azabicyclo[3.2.1]oct-3-yl)-2-(tyrosylamino)acetic acid → 2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid (322407-76-1)

Guidance literature:

With sodium tetrahydroborate; In water; N,N-dimethyl-formamide; for 1h; cooling;

DOI:10.7164/antibiotics.53.1282

Reference yield: 84.0%

benzyl chloroformate (501-53-1,94274-21-2) + 2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid (322407-76-1) → 2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-[(N-benzyloxycarbonyl)tyrosylamino]acetic acid (322405-00-5)

Guidance literature:

With sodium hydrogencarbonate; In water;

DOI:10.7164/antibiotics.53.1282

Reference yield:

2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-(tyrosylamino)acetic acid (322407-76-1) → [(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-((1S,2S,3S,4S,5S)-1,3,4,5-tetrahydroxy-4-hydroxymethyl-piperidin-2-yl)-acetic acid butyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / NaHCO₃ / H₂O

2: N-methylmorpholine; isobutylchloroformate / dimethylformamide / -20 °C

3: nBuONa

4: H₂ / Pd/C / methanol; H₂O

With 4-methyl-morpholine; hydrogen; sodium hydrogencarbonate; sodium butanolate; isobutyl chloroformate; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.53.1282

Downstream raw materials:

2-(4-hydroxymethyl-1,3,4,5-tetrahydroxy-2-piperidinyl)-2-[(N-benzyloxycarbonyl)tyrosylamino]acetic acid

[(S)-2-(4-Hydroxy-phenyl)-1-((3aS,4S,5S,6S,8R)-4,5,6-trihydroxy-5-hydroxymethyl-2-oxo-hexahydro-isoxazolo[2,3-a]pyridin-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester

((1S,2S,3S,4S,5S)-4-Acetoxymethyl-1,3,4,5-tetrahydroxy-piperidin-2-yl)-[(S)-2-benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-acetic acid butyl ester

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