4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester

Base Information

Chemical Name:4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester
CAS No.:176166-93-1
Molecular Formula:C₄₁H₅₅N₃O₂₀
Molecular Weight:909.896
Hs Code.:

4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester

Synonyms:4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester

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Chemical Property of 4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester

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Technology Process of 4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester

There total 11 articles about 4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl 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: 59.0%

: 176166-90-8
(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylic acid

: 758663-58-0
(S)-2-[((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

: 176166-93-1
4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester

Guidance literature:: With diethylphosphoryl cyanide; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1016/j.tet.2006.05.080

Reference yield: 59.0%

: 176166-90-8
(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylic acid

: (S)-2-[((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester; hydrochloride

: 176166-93-1
4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 16h; Ambient temperature;
DOI:10.1016/0040-4039(96)00094-9

Reference yield:

: 84856-53-1
3-phthalimido-4,5,7-tri-O-acetyl-2,6-anhydro-D-gulo-heptononitrile

: 176166-93-1
4,5,7-tri-O-acetyl-2,6-anhydro-3-tert-butoxycarbonylamino-D-glycero-D-gulo-hepturonyl β(1,3) 4,5,7-tri-O-acetyl-3-amino-2,6-anhydro-D-glycero-D-gulo-hepturonyl L-phenylalanine methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / hydrogen bromide; acetic acid / 3 h / 20 °C

2: 97 percent / Dowex 50W-X₈ H⁽¹⁺⁾ / 16 h / Heating

3: 95 percent / LiOH*H₂O / methanol; H₂O / 16 h / 60 °C

4: Et₃N / H₂O; dioxane / 3 h / 20 °C

5: Et₃N / dimethylformamide / 3 h / 20 °C

6: 4.81 g / pyridine / 12 h / 20 °C

7: 90 percent / hydrogen / Pd/C / ethyl acetate; ethanol / 16 h / 20 °C

8: 59 percent / diethylphosphoryl cyanide / dimethylformamide / 16 h / 20 °C

With pyridine; lithium hydroxide; diethylphosphoryl cyanide; Dowex 50W-X₈ H⁽¹⁺⁾; hydrogen bromide; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.05.080