* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Journal of Biological Chemistry, 1955, vol. 215, p. 403,413
[2] The Nucleic Acids, Bd. 3 <New York 1960> S. 323,
[3] Journal of Biological Chemistry, 1954, vol. 209, p. 1,13
[4] Acta Chemica Scandinavica (1947-1973), 1955, vol. 9, p. 251,254
2
[ 65-86-1 ]
[ 58-32-2 ]
Reference：
[1] Patent: CN106946887, 2017, A,
3
[ 65-86-1 ]
[ 5988-19-2 ]
Reference：
[1] Biochem.biophys.Acta, 1953, vol. 12, p. 223,227
4
[ 65-86-1 ]
[ 18592-13-7 ]
Reference：
[1] Patent: CN106831607, 2017, A,
5
[ 67-56-1 ]
[ 65-86-1 ]
[ 6153-44-2 ]
Yield
Reaction Conditions
Operation in experiment
92.9%
at 0 - 5℃; for 6 h; Reflux
In a 500 mL three-necked flask,Add orotic acid(15.6 g, 0.10 mol),Then 300 mL of anhydrous methanol was added,Stirring down to 0 ,Maintain the temperature 0 ~ 5 drop add thionyl chloride(10.9 mL, 0.15 mol),And the temperature was raised to reflux for 6 hours.Slightly cold,Vacuum drying solvent,Add 50 mL of anhydrous methanol to lift off.150 mL of methyl t-butyl ether was added,Stirred at room temperature for 1 hour,Filter,Methyl tert-butyl ether wash.dry,To obtain 15.8 g of compound 1,Yield 92.9percent.
91 g
for 30 h; Reflux
At room temperature, 78 g (0.5 mol) of orotic acid B0 (containing crystal water) and 5 ml of 98percent sulfuric acid were added to 200 ml of methanol and200 ml of dimethyl carbonate solution, refluxed for 30 h, tested with TLC until the reaction was complete, the resulting solid was concentrated, washed with heat Water washed, filtered by water, and then 300ml methanol recrystallization, hot air drying, get white solid, measured melting point: mp: 246 ° C to give 83 g (0.49 mol) of the whey acid ester (B1) in a molar yield of 98percent.
Reference：
[1] Patent: CN106831607, 2017, A, . Location in patent: Paragraph 0047
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1731 - 1740
[3] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 1123 - 1126
[4] Chemische Berichte, 1930, vol. 63, p. 1000
[5] Journal of the American Chemical Society, 1947, vol. 69, p. 675
[6] Bulletin des Societes Chimiques Belges, 1953, vol. 62, p. 611,617
[7] Biochimica et Biophysica Acta, 1957, vol. 23, p. 295,303
[8] Chemical Communications, 2015, vol. 51, # 26, p. 5618 - 5621
[9] Patent: CN106938987, 2017, A, . Location in patent: Paragraph 0048; 0049; 0050; 0051; 0052; 0053; 0054
Reference：
[1] Journal of the American Chemical Society, 2000, vol. 122, # 21, p. 5017 - 5024
11
[ 65-86-1 ]
[ 26830-94-4 ]
Yield
Reaction Conditions
Operation in experiment
62%
With trichlorophosphate In N,N-dimethyl-formamide at 110℃;
EXAMPLE 2 Preparation of (S)-6-(( 1 -amino- l-oxopropan-2-yl)amino)-2-(4-(4- fluorophenoxy) phenyl)pyrimidine-4-carboxamide (Cpd No. 1) Scheme 2 2,6-dichloropyrimidine-4-carbonyl chloride: A mixture of orotic acid mono hydrate (34.828 g, 200.0 mmol), phosphorus oxychloride (100 mL, 1092 mmol) and 20 drops of DMF were heated at 1 10°C overnight. After cooling, the dark mixture was diluted with 500 mL hexanes and vigorously stirred. The hexane layer was decanted and quickly washed with water (1 x 100 mL) then brine (1 x 100 mL) and dried over MgS04. The organics were filtered and carefully evaporated in vacuo to give 2,6-dichloropyrimidine-4-carbonyl chloride as a light yellow liquid (26.13 g, 123.6 mmol, 62percent yield). Ή NMR (400 MHz, CDC13): 7.93 (1 H, s).
62%
at 110℃;
A mixture of orotic acid mono hydrate (34.828 g, 200.0 mmol), phosphorus oxychloride ( 100 mL, 1092 mmol) and 20 drops of DMF were heated at 1 10°C overnight. After cooling, the dark mixture was treated with 500 mL hexanes and vigorously stirred. The hexane layer was decanted and quickly washed with water ( 1 x 100 mL) and brine ( 1 x 100 mL) and dried over MgS04. The organics were filtered and carefully evaporated in vacuo to give 2,6-dichloropyrimidine-4-carbonyl chloride as a light yellow liquid (26.13 g, 123.6 mmol, 62percent yield). ? NMR (400 MHz, CDC13): 7.93 ( 1 H, s).
62%
at 110℃;
A mixture of orotic acid mono hydrate (34.828 g, 200.0 mmol), phosphorus oxychlride (100 mL, 1092 mmol) and 20 drops of DMF were heated at 110°C overnight. After cooling, the dark mixture was diluted with 500 mL hexanes and vigorously stirred. The hexane layer was decanted and quickly washed with water (1 x 100 mL) then brine (1 x 100 mL) and dried over MgSO4. The organics were filtered and carefully evaporated in vacuo to give 2,6-dichloropyrimidine-4-carbonyl chloride as a light yellow liquid (26.13 g, 123.6 mmol, 62percent yield). 1H NMR (400 MHz, CDCl3): 7.93 (1 H, s).
62%
With trichlorophosphate In N,N-dimethyl-formamide at 110℃;
EXAMPLE 1 Synthesis of 2,6-dichloropyrimidine-4-carboxamide (Compound 3) A mixture of orotic acid mono hydrate (Compound 1) (34.828 g, 0.200 mol, Aldrich), phosphorus oxychloride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110°C overnight. After cooling the dark mixture was diluted with 500 mL hexanes and vigorously stirred. The hexane layer was decanted and quickly washed with water (1 x 100 mL) and brine (1 x 100 mL), and dried over MgSO4. The organics were filtered and carefully evaporated in vacuo to give Compound 2 as a light yellow liquid (26.13 g). Yield: 62percent. 1H NMR (400 MHz, CDCl3): δ 7.93 (s, 1 H).
62%
at 110℃;
A mixture of Compound 3 (34.828 g, 0.200 mol) (Aldrich), phosphorus oxychloride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110° C. overnight. After cooling the dark mixture was diluted with hexanes (500 mL) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over MgSO4. The organic layer was filtered and carefully evaporated in vacuo to give 26.13 g (62percent) of Compound 4 as a light yellow liquid. 1H NMR (400 MHz, CDCl3): δ 7.93 (s, 1H).
62%
With trichlorophosphate In N,N-dimethyl-formamide at 110℃;
A mixture of Compound 14 (34.83 g, 0.200 mol) (Aldrich), phosphorus oxychioride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110 °C overnight. After coolingthe dark mixture was diluted with hexanes (500 mL) and vigorously stuffed. The hexanelayer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried overMg504. The organic layer was filtered and carefully evaporated in vacuo to give 26.13 g(62percent) of Compound 15 as a light yellow liquid. 1H NMR (400 MHz, CDC13): ö 7.93 (s, 1H).
62%
at 110℃;
EXAMPLE 1 Synthesis of (S)-6-((l-amino-l-oxopropan-2-yl)amino)-2-chloropyrimidine-4-carboxamide (Compound 5) 5 A mixture of Compound 1 (34.828 g, 0.200 mol) (Aldrich), phosphorus oxychloride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110 °C overnight. After cooling the dark mixture was diluted with hexanes (500 mL) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over MgS04. The organic layer was filtered and carefully evaporated in vacuo to give 26.13 g (62percent) of Compound 2 as a light yellow liquid. ]H NMR (400 MHz, CDC13): δ 7.93 (s, 1 H).
62%
at 110℃;
A mixture of Compound 1 (34.828 g, 0.200 mol, Sigma-Aldrich), phosphorus oxychioride (100 mL, 1.092 mol) and 20 drops of DMF were heated at 110 °C overnight. After cooling to RT the dark mixture was diluted with hexanes (500 mL) and vigorouslystirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over Mg504. The organic layer was filtered and carefully evaporated in vacuo to give Compound 2 as a light yellow liquid (26.13 g). Yield 62percent1H NMR (400 MHz, CDC13): ö 7.93 (s, 1 H).
62%
at 110℃;
A mixture of Compound 1 (34.8 g, 0.20 mol, Aldrich), phosphorus oxychloride (100 mL, 1.09 mol) and 20 drops of DMF were heated at 110° C. overnight. After cooling to RT the dark mixture was diluted with hexanes (500 mL) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over MgSO4. The organic layer was filtered and carefully evaporated in vacuo to give Compound 2 as a light yellow liquid (26.13 g). Yield 62percent. 1H NMR (400 MHz, CDCl3): δ 7.93 (s, 1H).
62%
With trichlorophosphate In N,N-dimethyl-formamide at 110℃;
A mixture of Compound 1 (34.828 g, 0.200 mol) (Aldrich), phosphorus oxychloride (100 mE, 1.092 mol) and 20 drops of DMF were heated at 1100 C. overnight. After cooling the dark mixture was diluted with hexanes (500 mE) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mE), brine (100 mE) and dried over MgSO4. The organic layer was filtered and carefully evaporated in vacuo to give 26.13 g (62percent) of Compound 2 as a light yellow liquid. ‘H NMR (400 MHz, CDC13): ö 7.93 (s, 1H).
62%
at 110℃;
A mixture of 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid (Compound 146, 34.8 g, 0.20 mol, Aldrich), phosphorus oxychloride (100 mL, 1.09 mol) and 20 drops of DMF were heated at 110° C. overnight. After cooling to RT the dark mixture was diluted with hexanes (500 mL) and vigorously stirred. The hexane layer was decanted, quickly washed with water (100 mL), brine (100 mL) and dried over MgSO4. The organic layer was filtered and carefully evaporated in vacuo to give 2,6-dichloropyrimidine-4-carbonyl chloride (Compound 147) as a light yellow liquid (26.13 g). Yield 62percent. 1H NMR (400 MHz, CDCl3): δ7.93 (s, 1H).
Reference：
[1] Patent: WO2013/30665, 2013, A1, . Location in patent: Page/Page column 104; 105
[2] Patent: WO2013/72758, 2013, A1, . Location in patent: Page/Page column 93
[3] Patent: WO2014/135955, 2014, A1, . Location in patent: Paragraph 0311
[4] Patent: WO2015/31036, 2015, A1, . Location in patent: Page/Page column 72; 73
[5] Patent: US2015/175569, 2015, A1, . Location in patent: Paragraph 0321
[6] Patent: WO2015/99841, 2015, A1, . Location in patent: Page/Page column 62
[7] Patent: WO2015/112801, 2015, A1, . Location in patent: Page/Page column 66-67
[8] Patent: WO2015/123398, 2015, A1, . Location in patent: Page/Page column 63
[9] Patent: US2015/284383, 2015, A1, . Location in patent: Paragraph 0302; 0303
[10] Patent: US2017/8882, 2017, A1, . Location in patent: Paragraph 0260; 0261
[11] Patent: US2016/31873, 2016, A1, . Location in patent: Paragraph 1126; 1127
[12] Journal of the American Chemical Society, 2000, vol. 122, # 21, p. 5017 - 5024
[13] Patent: WO2016/97918, 2016, A1, . Location in patent: Page/Page column 111
[14] Letters in Drug Design and Discovery, 2017, vol. 14, # 3, p. 252 - 261
12
[ 65-86-1 ]
[ 26830-94-4 ]
Yield
Reaction Conditions
Operation in experiment
44%
Reflux
To a stirred POCl3 (CAUTION—toxic) (30 mL) was added in portions 2,6-dihydroxypyrimidine-4-carboxylic acid (6.0 g,38.5 mmol, CAS 65-86-1) at room temperature. After the addition, PCl5 (CAUTION—toxic) (26.4 mg, 0.127 mmol) was added in portions to the mixture at room temperature. After this addition, the reaction mixture was heated to reflux and stirred at reflux overnight.TLC indicated that the reaction was complete. Most of the excess POCl3 was removed by distillation, and the residue was distilled under reduced pressure to give compound 9 (bp: 158–160 C 1 mm/Hg pressure, 5 g, 44percent) as a yellow oil.
22%
at 20℃; for 3 h; Reflux
Step 2: 2,6-dichloro-pyrimidine-4-carboxylic acid chloride 20 g (0.13 mol) 2,6-dihydroxy-pyrimidine-4-carboxylic acid were refluxed together with 40 mL phosphorus oxychloride. After cooling to RT 60 g (0.29 mol) phosphorus-(V)-chloride were added and refluxing was continued for a further 3 h. The product was obtained by fractional distillation. Yield: 6.00 g (22percent of theoretical)
Reference：
[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3408 - 3413
[2] Patent: US2011/59954, 2011, A1, . Location in patent: Page/Page column 96
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 4, p. 441 - 445[4] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 4, p. 515 - 519
Stage #1: With trichlorophosphate In N,N-dimethyl-formamide for 3 h; Reflux Stage #2: at 0℃;
To a stirred suspension of orotic acid (CAS Number 65-86-1 , available from Alfa Aesar) (20.00 g, 128.140 mmol) in POCI3(75 ml) was added DMF (catalytic amount, -0.5 ml) at ambient temperature and the resulting reaction mixture was refluxed for 3 h. Excess of POC was removed by vacuum distillation after 3h of reflux. The obtained slurry was poured slowly in 5percent mixture of methanol in chloroform (200 ml) at 0°C and stirred for 30 min. The organic layer obtained was washed with saturated solution of NaHCC>3 (3 x 200 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure yielding methyl 2,6-dichloropyrimidine-4-carboxylate (19.00 g, 91 .800 mmol), which was used in the next step without further purification.
N-Fmoc-3-aminobenzoic acid(2R,3S)-N-Fmoc-3-amino-2-hydroxy-4-phenylbutyric acid[ No CAS ]
3-{(2R,3S)-3-[(S)-2-((S)-2-{(S)-2-Amino-3-[(2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-amino]-propionylamino}-3-methyl-butyrylamino)-4-methyl-pentanoylamino]-2-hydroxy-4-phenyl-butyrylamino}-benzoic acid[ No CAS ]
Example 22-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-3-methylbutanoic acid In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 13.13 ml (180 mmol) of thionyl chloride, and a water condenser, is placed 15.61 g (100 mmol) of <strong>[65-86-1]orotic acid</strong>. Addition of the thionyl chloride is completed with heating to about 55 C. over the course of about 45 minutes. When addition of the thionyl chloride is complete the mixture is heated and stirred for an additional 45 minutes. The water condenser is then replaced with a distillation side arm condenser and the crude mixture is distilled. The crude distillate in the receiving flask is then fractionally distilled to obtain the acyl chloride, 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl chloride (orotoyl chloride). This acyl chloride, 6.11 g (35 mmol), is put into a dry separatory funnel and combined with 50 mL of dry DCM for use in the next step of the reaction.
With thionyl chloride; at 55℃; for 1.5h;
Example 2; 2-(2,6-dioxo-l ,2,3,6-tetrahydropyrimidine-4-carboxamido)-3-methylbutanoic acid (Valine Orotate); <n="12"/>In a dry 2-necked, round bottomed flask, equipped with a magnetic stirrer and fixed with a separatory funnel, containing 13 13ml (180mmol) of thionyl chloride, and a water condenser, is placed 15 61 g (lOOmmol) of <strong>[65-86-1]orotic acid</strong> Addition of the thionyl chloride is completed with heating to about 55C over the course of about 45 minutes When addition of the thionyl chloride is complete the mixture is heated and stirred for an additional 45 minutes The water condenser is then replaced with a distillation side arm condenser and the crude mixture is distilled The crude distillate in the receiving flask is then fractionally distilled to obtain the acyl chloride, 2,6-dioxo- l,2,3,6-tetrahydropyrimidine-4-carbonyl chloride (orotoyl chloride) This acyl chloride, 6 1 Ig (35mmol), is put into a dry separatory funnel and combined with 5OmL of dry DCM for use in the next step of the reaction
With thionyl chloride;pyridine; for 20h;Reflux;
Example 8 Synthesis of 3-{3-[2-(orotinoyloxy)-5-chloro-4-pyridyloxycarbonyl]benzoyl}-1-ethoxymethyl-5-fluorouracil (Compound I-7) Thionyl chloride (35 mL) and pyridine (0.17 mL) were added to <strong>[65-86-1]orotic acid</strong> (6 g) and the mixture was refluxed for 20 hours. Subsequently, thionyl chloride was evaporated from the resulting reaction product, and the residue was obtained as <strong>[65-86-1]orotic acid</strong> acid chloride without purification. The resulting acid chloride (0.59 g) and Compound 8b (0.78 g) obtained in Reference Example 7 were dissolved in dioxane (10 mL). A solution of triethylamine (0.46 mL) and dioxane (5 mL) was then added to the above solution, and stirred at room temperature for 30 minutes. Unwanted materials were removed by filtration from the resulting reaction product, and the solvents were then evaporated. The solution was separated by ethyl acetate and purified water. The resulting residue was dried with magnesium sulfate, and the solvent was then evaporated. The resulting crude crystals were washed with a mixed solvent (10 mL) of n-hexane and ethyl acetate (3:1) to obtain Compound I-7 (859 mg; yield: 85%).1H-NMR (DMSOd6, deltaPPM) : 11.53 (1H, s), 11.49 (1H, s), 8.78 (1H, s), 8.71 (1H, s), 8.55 (2H, d, J = 7.9 Hz), 8.47 (1H, d, J = 6.6 Hz), 7.92 (1H, t, J = 7.9 Hz), 7.82 (1H, s), 6.35 (1H, s), 5.11 (2H, s), 3.58 (2H, q, J = 7.0 Hz), 1.12 (3H, t, J = 7.0 Hz)
orotic acid salt of (2S)-(4E)-N-methyl-5-[5-isopropoxypyridin-3-yl]-4-penten-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91.4%
In ethanol;Heating / reflux;
Example 13: Preparation of <strong>[65-86-1]orotic acid</strong> (uracil-6-carboxylic acid) salt of (2S)-(4E)-N- methyl-5-[3-(5-isopropoxypyridin)yl-4-penten-2-amine; Orotic acid (0.663 g, 4.25 mmol) was added to a solution of (2S)-(4E)-N-methyl-5-(3- (5-isopropoxypyridin)yl)-4-penten-2-amine (1.00 g, 4.27 mmol) in absolute ethanol (6 mL). The mixture was stirred and heated to near reflux, dissolving almost all solids. The solution was concentrated via rotary evaporation to an off-white foam. The residue was dissolved in ethyl acetate (7.8 mL) and absolute ethanol (1.8 mL), assisted by heating. The resulting solution was cooled to 5C, and additional ethyl acetate (6.8 mL) and ethanol (0.8 mL) were added. The mixture was heated, and the solution was allowed to cool to ambient temperature. The resulting mixture, containing fine, white solids was cooled to 5C for 48 hours. The solids were filtered, washed with cold ethyl acetate (3 x 3 mL) and dried under vacuum at 400C for 22 hours, followed by further drying at 500C for 3 hours to afford 1.523 g (91.4%) of a white powder, m.p. 128.5-132C (Fisher- Johns hot stage). Elemental analysis and NMR were both consistent with a 1: 1 stoichiometry. Calc'd for Ci4H22N2O C5H4N2O4: C, 58.45%; H, 6.71%; N, 14.35%.Found: C, 58.63%; H, 6.67%; N, 14.42%. The following NMR data were obtained:NMR: 1H (300 MHz, D2O): 8.16 (lH,d), 8.10 (lH,d), 7.45 (lH,t), 6.62 (lH,d), 6.35 (lH,m), 6.15 (lH,s), 4.76 (IH, septet), 3.46 (lH,m), 2.73 (3H,s), 2.64 (2H,m), 1.38 (3H,d), 1.36 (6H,d).
With sodium methylate; In methanol; at 20℃;Reflux;
General procedure: Orotic acid (0.32 g, 2.0 mmol) was dissolved in the minimum amount (20 mL) of specially dried methanol under dry nitrogen and added to sodium methoxide, prepared by reacting sodium (0.058 g, 2.5 mmol) with dry methanol (25 mL).The resulting mixture was first stirred at room temperature for half an hour and then refluxed giving a clear solution of sodium salt of <strong>[65-86-1]orotic acid</strong> within half an hour. Refluxing was continued for another 4-6 h with constant stirring. A hot methanol solution (20 mL) of trimethyltin(IV) chloride (0.398 g, 2.0 mmol)/tri-n-butyltin(IV) chloride (0.651 g, 2.0 mmol)/triphenyltin(IV) chloride (0.771 g, 2.0 mmol)/dimethyltin dichloride (0.220 g, 1.0 mmol)/diphenyltin dichloride (0.344 g, 1.0 mmol) was added to the solution of the preformed sodium salt of the acid. The resulting solution was further refluxed with constant stirring for another 14-18 h under dry nitrogen atmosphere. It was then centrifuged and filtered in order to remove the sodium chloride formed. The excess of solvent was removed under reduced pressure and the solid product thus obtained was recrystallized from either methanol-hexane or methanol-petroleum ether (b.p. 40-60 C) mixture (1:3 v/v).
With sodium hydroxide; In propan-1-ol; at 85℃;
FIG. 2 illustrates the synthesis of Doxorubicin Orotate. Orotic acid (1.0 g) was dissolved in 200 mL of water at 65 C. Potassium hydroxide (KOH) (1 eq) was added to the <strong>[65-86-1]orotic acid</strong> and the mixture was stirred at 850 C till a clear solution appeared. The solution was cooled, and the precipitate was collected by filtration to give a colorless solid (0.95 g), which was dried in vacuum for 24 hours. Mass Spectroghraphy suggested that the structure was potassium orotate.Potassium orotate (0.4 g) synthesized in the above step was dissolved in 150 mL of water at 650 C. The solution was de-aired in vacuum and protected with argon. Doxorubivin hydrochloride (1.0 g, 1 eq) was added and the resulting red solution was treated with excess amount of amberlite IR120 H resin for 2 hours at the same temperature. After filtration the solution was frozen in dry ice, and lyophilized to give 1.35 g of doxorubicin orotate (J-1220-13-II) as a red solid. Mass Spectroscopy (FIG. 3) and Nuclear Magnetic Resonance (FIG. 4) indicate that the structure is doxorubicin orotate.
3-({carboxymethyl-[2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-ethyl]-carbamoyl}-methyl)-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid methyl ester[ No CAS ]
(2R,3R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[3-(2,6-dimethoxy-pyrimidin-4-yl)-3-hydroxy-prop-1-ynyl]-3-methyl-2-vinyl-piperidine-1-carboxylic acid benzyl ester[ No CAS ]
7-(<i>tert</i>-butyl-dimethyl-silanyloxy)-5-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-(2,6-dimethoxy-pyrimidin-4-yl)-propyl]-8-methyl-hexahydro-imidazo[1,5-<i>a</i>]pyridin-3-ylideneamine[ No CAS ]
4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-(2,6-dimethoxy-pyrimidin-4-yl)-prop-1-ynyl]-2-formyl-3-methyl-piperidine-1-carboxylic acid benzyl ester[ No CAS ]
(5R,7R,8S,8aR)-3-[(Z)-Benzyloxycarbonylimino]-5-[3-(2,6-dimethoxy-pyrimidin-4-yl)-3-hydroxy-propyl]-7-hydroxy-8-methyl-hexahydro-imidazo[1,5-a]pyridine-2-carboxylic acid benzyl ester[ No CAS ]
4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-(2,6-dimethoxy-pyrimidin-4-yl)-prop-1-ynyl]-3-methyl-2-vinyl-piperidine-1-carboxylic acid benzyl ester[ No CAS ]
2-aminomethyl-4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-(2,6-dimethoxy-pyrimidin-4-yl)-propyl]-3-methyl-piperidine-1-carboxylic acid benzyl ester[ No CAS ]
(5R,7R,8S,8aR)-3-[(Z)-Benzyloxycarbonylimino]-5-[3-(2,6-dimethoxy-pyrimidin-4-yl)-3-oxo-propyl]-7-hydroxy-8-methyl-hexahydro-imidazo[1,5-a]pyridine-2-carboxylic acid benzyl ester[ No CAS ]
(5S,7S,8R,8aS)-7-Acetoxy-3-[(Z)-benzyloxycarbonylimino]-5-[3-(2,6-dimethoxy-pyrimidin-4-yl)-3-oxo-propyl]-8-methyl-hexahydro-imidazo[1,5-a]pyridine-2-carboxylic acid benzyl ester[ No CAS ]
(5S,7S,8R,8aS)-7-Acetoxy-5-[(E)-3-acetoxy-3-(2,6-dimethoxy-pyrimidin-4-yl)-allyl]-3-[(Z)-benzyloxycarbonylimino]-8-methyl-hexahydro-imidazo[1,5-a]pyridine-2-carboxylic acid benzyl ester[ No CAS ]
(2S,3R,4S,6R)-2-[(Z)-Benzylimino-methyl]-4-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-(2,6-dimethoxy-pyrimidin-4-yl)-prop-1-ynyl]-3-methyl-piperidine-1-carboxylic acid benzyl ester[ No CAS ]
2-(benzylamino-methyl)-4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-(2,6-dimethoxy-pyrimidin-4-yl)-prop-1-ynyl]-3-methyl-piperidine-1-carboxylic acid benzyl ester[ No CAS ]
3-benzyloxycarbonylimino-7-(<i>tert</i>-butyl-dimethyl-silanyloxy)-5-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-(2,6-dimethoxy-pyrimidin-4-yl)-propyl]-8-methyl-hexahydro-imidazo[1,5-<i>a</i>]pyridine-2-carboxylic acid benzyl ester[ No CAS ]
methyl 2-(2-{2-[2-({1-[6-(N'-tert-butoxycarbonylhydrazino)-2-diethylaminopyrimidine-4-carbonyl]-D-pyrrolidine-2-carbonyl}amino)acetylamino]-3-phenyl-L-propionylamino}-4-methyl-L-pentanoylamino)-3-methyl-L-butyrate[ No CAS ]
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