5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

Base Information

Chemical Name:5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester
CAS No.:178271-97-1
Molecular Formula:C₅₀H₆₀N₂O₁₃
Molecular Weight:897.032
Hs Code.:

5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

Synonyms:5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

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Chemical Property of 5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

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Technology Process of 5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

There total 16 articles about 5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl 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:

: 114676-59-4
(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride

: 178271-97-1
5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 84 percent / DIEA / H₂O / 12 h / Ambient temperature

2: 86 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 - 25 °C

3: 1.) sodium borohydride / 1.) 0 deg C, 5 min, 2.) reflux, 2 h

4: 73 percent / pyridine, H₂O₂ / CH₂Cl₂ / 1 h / Ambient temperature

5: 82 percent / K₂OsO₄, N-methylmorpholine N-oxide, H₂O / acetone; 2-methyl-propan-2-ol / 0 °C

6: LiOH / tetrahydrofuran / 4 h / Ambient temperature

7: 85 percent / EDC, HOBt / CH₂Cl₂ / 6 h / Ambient temperature

8: 10percent Pd/C / ethyl acetate; methanol / 2 h

9: HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; potassium osmate(VI); water; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1021/ja952265x

Reference yield:

: 84500-44-7
ethyl (2S,3R)-3-hydroxy-2-tert-butylcarbonylaminobutanoate

: 178271-97-1
5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 4A molecular sieves, TfOH / CH₂Cl₂ / 1 h / -15 °C

2: TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 85 percent / EDC, HOBt / CH₂Cl₂ / 6 h / Ambient temperature

4: 10percent Pd/C / ethyl acetate; methanol / 2 h

5: HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 6 h / Ambient temperature

With trifluorormethanesulfonic acid; 4 A molecular sieve; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;
DOI:10.1021/ja952265x

Reference yield:

: 153076-64-3
(R)-2,5-Dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester

: 178271-97-1
5-{(2R,3S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-3,4-dihydroxy-pyrrolidin-1-yl}-5-oxo-pentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / K₂OsO₄, N-methylmorpholine N-oxide, H₂O / acetone; 2-methyl-propan-2-ol / 0 °C

2: LiOH / tetrahydrofuran / 4 h / Ambient temperature

3: 85 percent / EDC, HOBt / CH₂Cl₂ / 6 h / Ambient temperature

4: 10percent Pd/C / ethyl acetate; methanol / 2 h

5: HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 6 h / Ambient temperature

With lithium hydroxide; potassium osmate(VI); water; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1021/ja952265x