(2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

Base Information

Chemical Name:(2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester
CAS No.:441778-50-3
Molecular Formula:C₄₃H₅₀N₂O₉
Molecular Weight:738.878
Hs Code.:

Synonyms:(2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

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Chemical Property of (2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

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Technology Process of (2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

There total 11 articles about (2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-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: 82.0%

: 2577-90-4
methyl (2S)-2-amino-3-phenylpropanoate

: 2,6-anhydro-3,4,7-tri-O-benzyl-5-tert-butoxycarbonylamido-5-deoxy-D-glycero-D-gulo-hepturonic acid lithium salt

: 441778-50-3
(2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

: 57039-37-9
(2R,3R,45,5R,6R)-methyl 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate

: 441778-50-3
(2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

Guidance literature:: Multi-step reaction with 9 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: 90 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

9.1: 82 percent / BOP; DIEA / dimethylformamide / 12 h / 20 °C

With pyridine; hydrogenchloride; lithium hydroxide; formic acid; sodium azide; 3 A molecular sieve; hydrogen sulfide; sodium hydride; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

: 61332-59-0
methyl 2,6-anhydro-5,7-O-benzylidene-D-glycero-L-manno-hepturonate

: 441778-50-3
(2,3,6-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

Guidance literature:: Multi-step reaction with 8 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: 90 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.33 h / 0 °C

8.1: 82 percent / BOP; DIEA / dimethylformamide / 12 h / 20 °C

With pyridine; hydrogenchloride; lithium hydroxide; sodium azide; 3 A molecular sieve; hydrogen sulfide; sodium hydride; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00020-2