(3R,8aS)-rel-Hexahydro-3-(hydroxyMethyl)-8a-Methyl-5-oxo-7H-oxazolo[3,2-a]pyrazine-7-carboxylic acid phenylMethyl ester

Base Information

• Chemical Name: (3R,8aS)-rel-Hexahydro-3-(hydroxyMethyl)-8a-Methyl-5-oxo-7H-oxazolo[3,2-a]pyrazine-7-carboxylic acid phenylMethyl ester
• CAS No.: 579467-28-0
• Molecular Formula: C16H20N2O5
• Molecular Weight: 320.34

Synonyms:(3R,8aS)-rel-Hexahydro-3-(hydroxyMethyl)-8a-Methyl-5-oxo-7H-oxazolo[3,2-a]pyrazine-7-carboxylic acid phenylMethyl ester;7H-Oxazolo[3,2-a]pyrazine-7-carboxylic acid, hexahydro-3-(hydroxymethyl)-8a-methyl-5-oxo-, phenylmethyl ester, (3R,8aS)-rel-

Chemical Property of (3R,8aS)-rel-Hexahydro-3-(hydroxyMethyl)-8a-Methyl-5-oxo-7H-oxazolo[3,2-a]pyrazine-7-carboxylic acid phenylMethyl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

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Technology Process of (3R,8aS)-rel-Hexahydro-3-(hydroxyMethyl)-8a-Methyl-5-oxo-7H-oxazolo[3,2-a]pyrazine-7-carboxylic acid phenylMethyl ester

There total 4 articles about (3R,8aS)-rel-Hexahydro-3-(hydroxyMethyl)-8a-Methyl-5-oxo-7H-oxazolo[3,2-a]pyrazine-7-carboxylic acid phenylMethyl 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: 55.0%

serinol (534-03-2) + [benzyloxycarbonyl-(2-oxo-propyl)-amino]-acetic acid (579466-96-9) → 3-hydroxymethyl-8a-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyrazine-7-carboxylic acid benzyl ester (579467-28-0)

Guidance literature:

With camphor-10-sulfonic acid; In toluene; for 20h; Heating;

DOI:10.1021/ol030065h

Reference yield:

ethyl 2-(benzyloxycarbonylamino)ethanoate (1145-81-9) → 3-hydroxymethyl-8a-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyrazine-7-carboxylic acid benzyl ester (579467-28-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 87 percent / potassium hydride / tetrahydrofuran / 16.5 h / 0 - 20 °C

2.1: osmium(VIII) oxide / tetrahydrofuran; H₂O / 0.17 h / 20 °C

2.2: 93 percent / sodium periodate / tetrahydrofuran; H₂O / 2 h / 20 °C

3.1: 80 percent / lithium hydroxide / tetrahydrofuran; H₂O / 2 h / 0 °C

4.1: 55 percent / camphorsulfonic acid / toluene / 20 h / Heating

With lithium hydroxide; osmium(VIII) oxide; camphor-10-sulfonic acid; potassium hydride; In tetrahydrofuran; water; toluene;

DOI:10.1021/ol030065h

Reference yield:

[benzyloxycarbonyl-(2-oxo-propyl)-amino]-acetic acid ethyl ester (579466-95-8) → 3-hydroxymethyl-8a-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyrazine-7-carboxylic acid benzyl ester (579467-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / lithium hydroxide / tetrahydrofuran; H₂O / 2 h / 0 °C

2: 55 percent / camphorsulfonic acid / toluene / 20 h / Heating

With lithium hydroxide; camphor-10-sulfonic acid; In tetrahydrofuran; water; toluene;

DOI:10.1021/ol030065h

upstream raw materials:

serinol

[benzyloxycarbonyl-(2-oxo-propyl)-amino]-acetic acid

ethyl 2-(benzyloxycarbonylamino)ethanoate

[benzyloxycarbonyl-(2-oxo-propyl)-amino]-acetic acid ethyl ester

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