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

Base Information

Chemical Name:(2,4,6-tri-O-benzyl-3-tert-butoxycarbonylamido-3-deoxy-β-D-glucopyranosyl)-C-carboxamido-3-N-(2,4,6-tri-O-benzyl-3-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester
CAS No.:441778-42-3
Molecular Formula:C₇₁H₇₉N₃O₁₄
Molecular Weight:1198.42
Hs Code.:

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

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

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

There total 11 articles about (2,4,6-tri-O-benzyl-3-tert-butoxycarbonylamido-3-deoxy-β-D-glucopyranosyl)-C-carboxamido-3-N-(2,4,6-tri-O-benzyl-3-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:

: 264616-06-0
2,6-anhydro-3,5,7-tri-O-benzyl-4-tert-butoxycarbonylamido-4-deoxy-D-glycero-D-gulo-hepturonic acid

: (S)-2-[((2R,3R,4S,5S,6R)-4-Amino-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

: 441778-42-3
(2,4,6-tri-O-benzyl-3-tert-butoxycarbonylamido-3-deoxy-β-D-glucopyranosyl)-C-carboxamido-3-N-(2,4,6-tri-O-benzyl-3-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 16h;
DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

: 185114-94-7,155417-78-0
1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

: 441778-42-3
(2,4,6-tri-O-benzyl-3-tert-butoxycarbonylamido-3-deoxy-β-D-glucopyranosyl)-C-carboxamido-3-N-(2,4,6-tri-O-benzyl-3-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 62 percent / TiBr₄ / CH₂Cl₂; ethyl acetate / 36 h / 20 °C

2.1: 57 percent / nitromethane / 1 h / 80 °C

3.1: NaOMe / methanol / 1 h / 20 °C / pH 11

3.2: NaOH / H₂O / 12 h / Heating

4.1: 1.30 g / 12 h / Heating

5.1: H₂S / pyridine; H₂O / 14 h / 20 °C

6.1: 1.02 g / Et₃N / methanol / 12 h / 20 °C

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

7.2: 64 percent / methanol / 2 h / 20 °C

8.1: 97 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.33 h / 20 °C

9.1: 55 percent / BOP; DIEA / dimethylformamide / 12 h / 20 °C

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

11.1: 138 mg / BOP; DIEA / dimethylformamide / 16 h / 20 °C

With hydrogenchloride; lithium hydroxide; hydrogen sulfide; sodium methylate; titanium(IV) bromide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; nitromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00020-2

Reference yield:

: (2R,3R,4S,5S,6R)-4-Amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid methyl ester

: 441778-42-3
(2,4,6-tri-O-benzyl-3-tert-butoxycarbonylamido-3-deoxy-β-D-glucopyranosyl)-C-carboxamido-3-N-(2,4,6-tri-O-benzyl-3-deoxy-β-D-glucopyranosyl)-C-carboxamido-N-L-phenylalanine methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1.02 g / Et₃N / methanol / 12 h / 20 °C

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

2.2: 64 percent / methanol / 2 h / 20 °C

3.1: 97 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.33 h / 20 °C

4.1: 55 percent / BOP; DIEA / dimethylformamide / 12 h / 20 °C

5.1: 4 N HCl / ethyl acetate / 1 h / 0 °C

6.1: 138 mg / BOP; DIEA / dimethylformamide / 16 h / 20 °C

With hydrogenchloride; lithium hydroxide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00020-2