Technology Process of (4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid
There total 1 articles about (4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 13 steps
1: 72 percent / TsOH
2: LDA
3: aq. H2O2
4: OsO4; NMO
5: TsOH / acetone
6: 73 percent / NH2NH2; 10 percent Pd/C / methanol / Heating
7: NaH / tetrahydrofuran; dimethylformamide
8: H2 / Pd(OH)2 / ethanol / 2585.74 Torr
9: 97 percent / NaH / tetrahydrofuran; dimethylformamide
10: 24 percent / aq. cerium(IV) ammonium nitrate / acetonitrile
11: 80 percent / aq. LiOOH / tetrahydrofuran
12: 90 percent / DMAP / tetrahydrofuran / Heating
13: 99 percent / aq. LiOH / tetrahydrofuran
With
dmap; lithium hydroxide; palladium on activated charcoal; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; lithium hydroperoxide; hydrogen; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; hydrazine; lithium diisopropyl amide;
palladium dihydroxide;
In
tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetone; acetonitrile;
1: Cyclization / 2: Metallation / 2: selenylation / 3: oxidative olefination / 4: Oxidation / 5: transacetalization / 6: Ring cleavage / 7: protection / 8: Hydrogenolysis / 9: Methylation / 10: deprotection / 11: Hydrolysis / 12: Acylation / 13: Hydrolysis;
DOI:10.1021/ja992135e
- Guidance literature:
-
Multi-step reaction with 4 steps
1: diphenyl phosphorazidate, Et3N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.
2: TMSOTf / CH2Cl2 / 1 h / 0 °C
3: H2, AcOH / 5percent Pd/C / methanol; H2O / 60 h / Ambient temperature
4: p-TsaOH*H2O / 3 h / Ambient temperature
With
trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; hydrogen; toluene-4-sulfonic acid; acetic acid; triethylamine;
palladium on activated charcoal;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)79444-5
- Guidance literature:
-
Multi-step reaction with 3 steps
1: diphenyl phosphorazidate, Et3N / dimethylformamide / 1) 1h, 0 deg C 2) 41h, r.t.
2: TMSOTf / CH2Cl2 / 1 h / 0 °C
3: H2, AcOH / 5percent Pd/C / methanol; H2O / 60 h / Ambient temperature
With
trimethylsilyl trifluoromethanesulfonate; diphenyl phosphoryl azide; hydrogen; acetic acid; triethylamine;
palladium on activated charcoal;
In
methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)79444-5
