(2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate
CAS No.:176166-89-5
Molecular Formula:C₂₆H₃₃NO₁₂
Molecular Weight:551.548
Hs Code.:

Synonyms:(2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate

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Chemical Property of (2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate

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Technology Process of (2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate

There total 6 articles about (2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate 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:

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

: 176166-89-5
(2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 6 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

With pyridine; lithium hydroxide; Dowex 50W-X₈ H⁽¹⁺⁾; hydrogen bromide; acetic acid; triethylamine; In 1,4-dioxane; methanol; water; 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

: 176166-89-5
(2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 5 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

With pyridine; lithium hydroxide; Dowex 50W-X₈ H⁽¹⁺⁾; triethylamine; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.05.080

Reference yield:

: (2R,3R,4R,5S,6R)-3-tert-Butoxycarbonylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carboxylic acid

: 176166-89-5
(2R,3R,4R,5S,6R)-2-oxo-2-phenylethyl 4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 4.81 g / pyridine / 12 h / 20 °C

With pyridine; triethylamine; In N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.05.080