N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile

Base Information

• Chemical Name: N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile
• CAS No.: 138892-01-0
• Molecular Formula: C₂₈H₃₉ClN₂O₇
• Molecular Weight: 551.08

Synonyms:N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile

Chemical Property of N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile

Chemical Property:

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Technology Process of N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile

There total 10 articles about N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile 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: 84.0%

trimethylsilyl cyanide (7677-24-9) + N-(4-Chlorobenzylidene)-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine (138891-99-3) → N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile (138892-01-0) + N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-D-(4-chlorophenyl)glycinonitrile (138892-01-0)

Guidance literature:

With tin(IV) chloride; In tetrahydrofuran; at -18 ℃; for 15h; Yields of byproduct given;

DOI:10.1055/s-1991-26641

Reference yield: 84.0%

trimethylsilyl cyanide (7677-24-9) + N-(4-Chlorobenzylidene)-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine (138891-99-3) → N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile (138892-01-0) + N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-D-(4-chlorophenyl)glycinonitrile (138892-01-0)

Guidance literature:

With tin(IV) chloride; In tetrahydrofuran; at -18 ℃; for 15h; Yields of byproduct given;

DOI:10.1055/s-1991-26641

Reference yield:

2,3,4-Tri-O-acetyl-α-D-arabinopyranosyl azide → N-(2,3,4-Tri-O-pivaloyl-α-D-arabinopyranosyl)-L-(4-chlorophenyl)glycinonitrile (138892-01-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / 1N NaOMe/MeOH / methanol / 2 h / Ambient temperature

2: 89 percent / pyridine / 24 h / Ambient temperature

3: 88 percent / H₂ / Raney Ni / methanol; CH₂Cl₂ / 3 h / 760 Torr / Ambient temperature

4: 92 percent / AcOH / heptane / 0.5 h / Ambient temperature

5: 84 percent / SnCl₄ / tetrahydrofuran / 15 h / -18 °C

With pyridine; methanol; hydrogen; sodium methylate; tin(IV) chloride; acetic acid; nickel; In tetrahydrofuran; methanol; n-heptane; dichloromethane;

DOI:10.1055/s-1991-26641

upstream raw materials:

trimethylsilyl cyanide

N-(4-Chlorobenzylidene)-2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine

2,3,4-tri-O-pivaloyl-β-D-arabinopyranosylamine

α-D-Arabinopyranosyl azide

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