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

Base Information

• Chemical Name: O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-threonine methyl ester
• CAS No.: 1013026-16-8
• Molecular Formula: C₃₇H₄₆N₂O₁₁
• Molecular Weight: 694.779

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

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

Chemical Property:

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

There total 2 articles about O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-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: 45.0%

2-deoxy-2-nitro-3,4,6-tri-O-benzyl-D-galactal + (2S,3S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-hydroxybutanoate (113525-91-0) → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-threonine methyl ester (1013026-16-8) + N-(tert-butoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester (552888-37-6)

Guidance literature:

With N,N'-bis[(8a,9S)-65-methoxy-9-cinchonanyl]thiourea; In acetonitrile; for 16h; diastereoselective reaction; Reflux; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01962

Reference yield:

3,4,6-tri-O-benzyl-D-galactal → O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-threonine methyl ester (1013026-16-8) + N-(tert-butoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester (552888-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic anhydride; nitric acid / 0.08 h / -30 °C / Inert atmosphere

1.2: 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: N,N'-bis[(8a,9S)-65-methoxy-9-cinchonanyl]thiourea / acetonitrile / 16 h / Reflux; Inert atmosphere

With N,N'-bis[(8a,9S)-65-methoxy-9-cinchonanyl]thiourea; nitric acid; acetic anhydride; In acetonitrile;

DOI:10.1021/acs.orglett.6b01962

Reference yield:

O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-threonine methyl ester (1013026-16-8) → C37H48N2O9*ClH

Guidance literature:

With hydrogenchloride; acetic acid; zinc; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2007.12.078

upstream raw materials:

(2S,3S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-hydroxybutanoate

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