(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

Base Information

• Chemical Name: (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
• CAS No.: 176166-91-9
• Molecular Formula: C₂₈H₃₈N₂O₁₂
• Molecular Weight: 594.616

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 8 articles about (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 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: 86.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + (2R,3R,4R,5S,6R)-4,5-diacetoxy-6-(acetoxymethyl)-3-(tert-butoxycarbonylamino)-tetrahydro-2H-pyran-2-carboxylic acid (176166-90-8) → (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 (176166-91-9)

Guidance literature:

With diethylphosphoryl cyanide; triethylamine; for 16h; 0 deg C to r.t.;

DOI:10.1016/0040-4039(96)00094-9

Reference yield:

3-phthalimido-4,5,7-tri-O-acetyl-2,6-anhydro-D-gulo-heptononitrile (84856-53-1) → (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 (176166-91-9)

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: 86 percent / diethylphosphoryl cyanide; Et₃N / dimethylformamide / 0 - 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

Reference yield:

4,5,7-Tri-O-acetyl-2,6-anhydro-3-desoxy-3-phthalimido-D-glycero-D-gulo-heptonamid (130197-65-8) → (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 (176166-91-9)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; 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

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate

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

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

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

Downstream raw materials:

(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

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

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

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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