(2R,2R'')-benzyl 2-(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate

Base Information

Chemical Name:(2R,2R'')-benzyl 2-(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate
CAS No.:128753-69-5
Molecular Formula:C₅₂H₆₇N₄O₁₈P
Molecular Weight:1067.09
Hs Code.:

(2R,2R'')-benzyl 2-<N-(2'-N-acetyl-1'-α-O-<<2''-carbobenzoxy-2''-(pentyloxy)ethoxy>(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate

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Chemical Property of (2R,2R'')-benzyl 2-(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate

Chemical Property:

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Technology Process of (2R,2R'')-benzyl 2-(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate

There total 19 articles about (2R,2R'')-benzyl 2-(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate 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:

: 10036-64-3
N-acetyl-D-glucosamine

: 128753-69-5,128820-78-0
(2R,2R'')-benzyl 2-(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate

Guidance literature:: Multi-step reaction with 7 steps

2: 83 percent / NaH / tetrahydrofuran / 18 h / Heating

3: 66 percent / N-methylmorpholine, hydroxybenzotriazole, <(diisopropyl)ethyl>carbodiimide hydrochloride / CH₂Cl₂ / 18 h / Ambient temperature

4: 2) pyridine / 1) EtOH, H₂O, HOAc, reflux, 6 h, 2) 80 deg C, 18 h

5: 1) (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium hexafluorophosphate, H₂, 2) NaHCO₃, I₂ / 1) THF, reflux, 6 h, 2) THF, water, 10 min

6: 26.2 percent / diisopropylethylamine / acetonitrile / 1 h / Ambient temperature

7: 1) 1H-tetrazole, 2) tert-butyl hydroperoxide / 1) acetonitrile, 1.25 h, RT, 2) 2 h

With 4-methyl-morpholine; pyridine; 1H-tetrazole; tert.-butylhydroperoxide; <(diisopropyl)ethyl>carbodiimide hydrochloride; (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium hexafluorophosphate; hydrogen; iodine; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo00303a028

Reference yield:

: 61348-28-5
(2R)-5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid

: 128753-69-5,128820-78-0
(2R,2R'')-benzyl 2-(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate

Guidance literature:: Multi-step reaction with 8 steps

1: 85.6 percent / NaHCO₃ / dimethylformamide / 18 h / 60 °C

2: 1) HCl, 2) N-methylmorpholine, N-hydroxybenzotriazole, <(dimethylamino)propyl>ethylcarbodiimide hydrochloride / 1) dioxane, ice bath, 15 min, 2) CH₂Cl₂, RT, 19 h

3: HCl / dioxane / 1 h / Ambient temperature

4: 66 percent / N-methylmorpholine, hydroxybenzotriazole, <(diisopropyl)ethyl>carbodiimide hydrochloride / CH₂Cl₂ / 18 h / Ambient temperature

5: 2) pyridine / 1) EtOH, H₂O, HOAc, reflux, 6 h, 2) 80 deg C, 18 h

6: 1) (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium hexafluorophosphate, H₂, 2) NaHCO₃, I₂ / 1) THF, reflux, 6 h, 2) THF, water, 10 min

7: 26.2 percent / diisopropylethylamine / acetonitrile / 1 h / Ambient temperature

8: 1) 1H-tetrazole, 2) tert-butyl hydroperoxide / 1) acetonitrile, 1.25 h, RT, 2) 2 h

With 4-methyl-morpholine; pyridine; 1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; <(diisopropyl)ethyl>carbodiimide hydrochloride; (1,5-cyclooctadiene)bis(methyldiphenylphosphine)iridium hexafluorophosphate; hydrogen; iodine; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00303a028

Reference yield:

: 110-53-2
1-Bromopentane

: 128753-69-5,128820-78-0
(2R,2R'')-benzyl 2-(benzyloxy)phosphoryl>-4',6'-di-O-acetylmuramyl-L-alanyl)amino>-4-cyanobutanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / NaH / dimethylformamide / 3 h / 70 °C

2: 76.5 percent / 12 N HCl / ethanol; H₂O / 18 h / Heating

3: 1) NaIO₄, 2) Ag₂O / 1) THF, water, 50 deg C, 1 h, 2) RT, 18 h

4: 24.4 percent / sodium bicarbonate / dimethylformamide / 15 h / 70 °C

5: 1) 1H-tetrazole, 2) tert-butyl hydroperoxide / 1) acetonitrile, 1.25 h, RT, 2) 2 h

With 1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; sodium hydride; sodium hydrogencarbonate; silver(l) oxide; In ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00303a028