N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

Base Information

Chemical Name:N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)
CAS No.:132621-15-9
Molecular Formula:C₆₄H₆₇N₄O₁₆S₂*Na
Molecular Weight:1235.37
Hs Code.:

N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

Synonyms:N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

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Chemical Property of N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

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Technology Process of N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

There total 22 articles about N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester) 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: 80.0%

: 132621-14-8
N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

: 132621-15-9
N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

Guidance literature:: With sulfur trioxide pyridine complex; In N,N-dimethyl-formamide;
DOI:10.1021/jo00008a040

Reference yield:

: 100-39-0
benzyl bromide

: 132621-15-9
N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

Guidance literature:: Multi-step reaction with 11 steps

1: 84 percent / Bu₄NI, NaH / tetrahydrofuran / 5 h / 0 deg C to r.t.

2: 74 percent / TFA / tetrahydrofuran / 0.25 h / 0 °C

3: 1) (Bu₃Sn)2O, 2) Bu₄NBr / 1) toluene, reflux, 4h, 2) 80 deg C

4: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

5: 96 percent / AcOH, Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

6: 1) 4A molecular sieves, 2) DBU / 1) CH₂Cl₂,r.t., 4h, 2) -40 deg C, 3h

7: 42 percent / a) 4-A molecular sieves b) BF₃*Et₂O / CH₂Cl₂ / -40 °C / a) 4h, b) 50 min

8: 80 percent / 24 h / Ambient temperature

9: aq. KOH / propan-2-ol / 96 h

10: 70 percent / (EtO)2P(O)CN, Et₃N / dimethylformamide / 2 h

11: 80 percent / pyridine*SO₃ / dimethylformamide

With dmap; potassium hydroxide; diethyl cyanophosphonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; bis(tri-n-butyltin)oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo00008a040

Reference yield:

: 128359-95-5
(2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

: 132621-15-9
N-<(2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-glucopyranosyl)oxy>-5-(hydroxymethyl)-L-prolyl>-6-aminopenicillinic acid bis(phenylmethyl ester)

Guidance literature:: Multi-step reaction with 14 steps

1: 66 percent / Ambient temperature; electrolysis (0.5 A); other proline derivatives; dependence of yiled from protection groups

2: 86 percent / conc. H₂SO₄ / acetic acid; CH₂Cl₂ / 2 h / 0 °C

3: 72 percent / camphorsulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

4: 67 percent / Bu₆Sn₂ / benzene / 4 h / Irradiation

5: CH₂Cl₂ / a) 0 deg C, 5 min, b) r.t., 3.5h

6: 10percent aq.NaHCO₃ / CH₂Cl₂ / Ambient temperature

7: 1) O₃, 2) NaBH₄ / 1) MeOH, CH₂Cl₂, -78 deg C, 2) a) to 0 deg C, b) 0 deg C, 45 min

8: 91 percent / Ag₂O / CH₂Cl₂ / Heating; a) 10h, b) 12h

9: 100 percent / NaOMe / methanol / 1 h / Ambient temperature

10: 42 percent / a) 4-A molecular sieves b) BF₃*Et₂O / CH₂Cl₂ / -40 °C / a) 4h, b) 50 min

11: 80 percent / 24 h / Ambient temperature

12: aq. KOH / propan-2-ol / 96 h

13: 70 percent / (EtO)2P(O)CN, Et₃N / dimethylformamide / 2 h

14: 80 percent / pyridine*SO₃ / dimethylformamide

With potassium hydroxide; sodium tetrahydroborate; diethyl cyanophosphonate; 4 A molecular sieve; sulfuric acid; camphor-10-sulfonic acid; sodium methylate; bis(tri-n-butyltin); sulfur trioxide pyridine complex; sodium hydrogencarbonate; ozone; triethylamine; silver(l) oxide; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; benzene;
DOI:10.1021/jo00008a040