methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside
CAS No.:334002-71-0
Molecular Formula:C₁₇H₂₂FN₃O₇
Molecular Weight:399.376
Hs Code.:

Synonyms:methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside

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Chemical Property of methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside

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Technology Process of methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside

There total 9 articles about methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside 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: 74.0%

: 334002-70-9
methyl 2,3-deoxy-3-(azido)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside

: 334002-71-0
methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside

Guidance literature:: With water; triphenylphosphine; In tetrahydrofuran; at 55 ℃; for 48h;
DOI:10.1021/jo0352068

Reference yield:

: 40299-08-9
methyl 2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside

: 334002-71-0
methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / p-toluenesulfonic acid / dimethylformamide / Heating

2: 85 percent / DMSO; acetic anhydride / 20 °C

3: 79 percent / L-Selectride / tetrahydrofuran / 4 h / -78 °C

4: 91 percent / triethylamine / CH₂Cl₂ / 18 h / 20 °C

5: 92 percent / sodium azide; tetrabutylammonium hydrogen sulfate / dimethylformamide / 36 h / 100 °C

6: 99 percent / KOH / methanol; H₂O / 24 h / Heating

7: 95 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

8: 74 percent / triphenylphosphine; H₂O / tetrahydrofuran / 48 h / 55 °C

With potassium hydroxide; sodium azide; water; tetra(n-butyl)ammonium hydrogensulfate; acetic anhydride; L-Selectride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 8: Staudinger reduction;
DOI:10.1021/jo0352068

Reference yield:

: 334002-51-6
methyl 2,3-deoxy-3-(azido)-4,6-O-isopropylidene-β-D-glucosamine

: 334002-71-0
methyl 2,3-deoxy-3-(amino)-4,6-O-isopropylidene-N-(2-fluoro-5-nitro-benzamido)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

2: 74 percent / triphenylphosphine; H₂O / tetrahydrofuran / 48 h / 55 °C

With water; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; In tetrahydrofuran; dichloromethane; 2: Staudinger reduction;
DOI:10.1021/jo0352068