(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

Base Information

Chemical Name:(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
CAS No.:758663-58-0
Molecular Formula:C₂₃H₃₀N₂O₁₀
Molecular Weight:494.499
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 9 articles about (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 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:

: 176166-91-9
(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-5-(tert-butoxycarbonylamino)-6-(1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-tetrahydro-2H-pyran-3,4-diyl diacetate

: 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

Guidance literature:: With hydrogenchloride; In ethyl acetate; at 20 ℃;
DOI:10.1016/j.tet.2006.05.080

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 9 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: 86 percent / diethylphosphoryl cyanide; Et₃N / dimethylformamide / 0 - 20 °C

9: HCl / ethyl acetate / 20 °C

With pyridine; hydrogenchloride; 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

Reference yield:

: 130197-65-8
4,5,7-Tri-O-acetyl-2,6-anhydro-3-desoxy-3-phthalimido-D-glycero-D-gulo-heptonamid

: 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

Guidance literature:: Multi-step reaction with 8 steps

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

2: 95 percent / LiOH*H₂O / methanol; H₂O / 16 h / 60 °C

3: Et₃N / H₂O; dioxane / 3 h / 20 °C

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

5: 4.81 g / pyridine / 12 h / 20 °C

6: 90 percent / hydrogen / Pd/C / ethyl acetate; ethanol / 16 h / 20 °C

7: 86 percent / diethylphosphoryl cyanide; Et₃N / dimethylformamide / 0 - 20 °C

8: HCl / ethyl acetate / 20 °C

With pyridine; hydrogenchloride; lithium hydroxide; diethylphosphoryl cyanide; Dowex 50W-X₈ H⁽¹⁺⁾; hydrogen; 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