(4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane

Base Information

Chemical Name:(4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane
CAS No.:211994-31-9
Molecular Formula:C₂₁H₂₂N₈O₈
Molecular Weight:514.454
Hs Code.:

Synonyms:(4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane

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Chemical Property of (4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane

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Technology Process of (4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane

There total 2 articles about (4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane 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:

: 63700-05-0
1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol

: 211994-31-9
(4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / K₂CO₃ / dimethylformamide / 16 h / 110 °C

2: 1.) diisopropoxy azodicarboxylate, Ph₃P, 2.) diphenyl phosphorazidate / 1.) THF, 2.) THF, room temp.

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide;
DOI:10.1021/jo971562c

Reference yield:

: (R)-1-{(4R,5R)-5-[(R)-1-Hydroxy-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(4-nitro-phenoxy)-ethanol

: 211994-31-9
(4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; Multistep reaction; 1.) THF, 2.) THF, room temp.;
DOI:10.1021/jo971562c

Reference yield:

: 211994-31-9
(4R,5R)-4,5-Bis-[(S)-1-azido-2-(4-nitro-phenoxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane

: ((1R,3R,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: acetyl chloride / methanol / Ambient temperature

2: 92 percent / H₂ / Pd/C / ethyl acetate / 3 h

3: 70 percent / tetrahydrofuran / 22 h / 55 °C

4: Bu₃SnH, 2,2'-azobis(isobutyronitrile) / toluene / 0.83 h / Heating

5: 56 percent / 1.) Ba(OH)2

6: 0.052 g / PPh₃, DEAD / tetrahydrofuran

7: 82 percent / LiOH / ethanol; H₂O; tetrahydrofuran / 1 h

With barium dihydroxide; lithium hydroxide; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; acetyl chloride; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; ethyl acetate; toluene;
DOI:10.1021/jo971562c