N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester

Base Information

• Chemical Name: N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester
• CAS No.: 552888-40-1
• Molecular Formula: C₃₉H₄₃N₃O₉S
• Molecular Weight: 729.851

Synonyms:N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester

Chemical Property of N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester

Chemical Property:

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Technology Process of N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester

There total 4 articles about N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl 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: 82.0%

phenyl isothiocyanate (103-72-0) + O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester (552888-38-7) → N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester (552888-40-1)

Guidance literature:

In ethanol; for 12h; Heating;

DOI:10.1002/ejoc.200390142

Reference yield:

N-(tert-butoxycarbonyl)-l-threonine methyl ester (60538-19-4,79479-07-5,96099-84-2,113525-91-0) → N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester (552888-40-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / 3 Angstroem MS; potassium tert-butoxide / toluene; tetrahydrofuran

2: 89 percent / trifluoroacetic acid; CH₂Cl₂ / 12 h / 20 °C

3: 82 percent / ethanol / 12 h / Heating

With 3 Angstroem MS; potassium tert-butylate; In tetrahydrofuran; ethanol; dichloromethane; toluene; trifluoroacetic acid;

DOI:10.1002/ejoc.200390142

Reference yield:

3,4,6-tri-O-benzyl-2-nitro-D-galactal (211621-55-5) → N-(phenylaminothiocarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester (552888-40-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / 3 Angstroem MS; potassium tert-butoxide / toluene; tetrahydrofuran

2: 89 percent / trifluoroacetic acid; CH₂Cl₂ / 12 h / 20 °C

3: 82 percent / ethanol / 12 h / Heating

With 3 Angstroem MS; potassium tert-butylate; In tetrahydrofuran; ethanol; dichloromethane; toluene; trifluoroacetic acid;

DOI:10.1002/ejoc.200390142

upstream raw materials:

phenyl isothiocyanate

O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester

N-(tert-butoxycarbonyl)-l-threonine methyl ester

3,4,6-tri-O-benzyl-2-nitro-D-galactal

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