(4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

Base Information

• Chemical Name: (4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester
• CAS No.: 264616-09-3
• Molecular Formula: C₄₃H₆₅N₅O₂₄
• Molecular Weight: 1036.01

Synonyms:(4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

Chemical Property of (4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

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Technology Process of (4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

There total 21 articles about (4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl 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: 67.0%

C67H89N5O36 → (4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester (264616-09-3)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

methyl 2,6-anhydro-5,7-O-benzylidene-D-glycero-L-manno-hepturonate (61332-59-0) → (4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester (264616-09-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: NaH / dimethylformamide / 12 h / 20 °C

1.2: 93 percent / methanol / 2 h / 20 °C / pH 11

2.1: 94 percent / HCl; NaBH₃CN; 3 Angstroem molecular sieves / ethyl acetate; tetrahydrofuran / 0.33 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 2 h / -15 °C

4.1: 1.20 g / NaN₃ / dimethylformamide / 12 h / 20 °C

5.1: H₂S / pyridine; H₂O / 1 h / 20 °C

6.1: 1.31 g / Et₃N / methanol / 12 h / 20 °C

7.1: H₂ / Pd(OH)2 / methanol / 16 h / 20 °C

8.1: 212 mg / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

9.1: BOP; DIEA / dimethylformamide / 16 h / 20 °C

10.1: 4 N HCl / ethyl acetate / 1 h / 0 °C

11.1: BOP; DIEA / dimethylformamide / 12 h / 20 °C

12.1: 4 N HCl / ethyl acetate / 1 h / 0 °C

13.1: BOP; DIEA / dimethylformamide / 12 h / 20 °C

With pyridine; hydrogenchloride; lithium hydroxide; sodium azide; 3 A molecular sieve; hydrogen sulfide; hydrogen; sodium hydride; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

(2R,3R,45,5R,6R)-methyl 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate (57039-37-9) → (4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-4-N-(4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester (264616-09-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 61 percent / HCO₂H / 1 h / 20 °C

2.1: NaH / dimethylformamide / 12 h / 20 °C

2.2: 93 percent / methanol / 2 h / 20 °C / pH 11

3.1: 94 percent / HCl; NaBH₃CN; 3 Angstroem molecular sieves / ethyl acetate; tetrahydrofuran / 0.33 h / 20 °C

4.1: pyridine / CH₂Cl₂ / 2 h / -15 °C

5.1: 1.20 g / NaN₃ / dimethylformamide / 12 h / 20 °C

6.1: H₂S / pyridine; H₂O / 1 h / 20 °C

7.1: 1.31 g / Et₃N / methanol / 12 h / 20 °C

8.1: H₂ / Pd(OH)2 / methanol / 16 h / 20 °C

9.1: 212 mg / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

10.1: BOP; DIEA / dimethylformamide / 16 h / 20 °C

11.1: 4 N HCl / ethyl acetate / 1 h / 0 °C

12.1: BOP; DIEA / dimethylformamide / 12 h / 20 °C

13.1: 4 N HCl / ethyl acetate / 1 h / 0 °C

14.1: BOP; DIEA / dimethylformamide / 12 h / 20 °C

With pyridine; hydrogenchloride; lithium hydroxide; formic acid; sodium azide; 3 A molecular sieve; hydrogen sulfide; hydrogen; sodium hydride; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00020-2

upstream raw materials:

2,6-anhydro-5-tert-butoxycarbonylamido-5-deoxy-D-glycero-D-gulo-hepturonic acid

methyl 2,6-anhydro-5,7-O-benzylidene-D-glycero-L-manno-hepturonate

(2R,3R,45,5R,6R)-methyl 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate

methyl 2,6-anhydro-3,4,7-tri-O-benzyl-D-glycero-L-manno-hepturonate

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