(S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

Base Information

• Chemical Name: (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester
• CAS No.: 178272-03-2
• Molecular Formula: C₆₀H₇₃N₃O₁₃
• Molecular Weight: 1044.25

Synonyms:(S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

Chemical Property of (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

Chemical Property:

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Technology Process of (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

There total 7 articles about (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic 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: 77.0%

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) + (2S,3S)-2-Amino-4-benzyloxy-3-hydroxy-N-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-butyramide → (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester (178272-03-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; 1.) 0 deg C, 20 min, 2.) 0 deg C to RT, 9 h;

DOI:10.1021/ja952265x

Reference yield:

(1R,2R)-trans-2-azidocyclohexanol (110716-78-4) → (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester (178272-03-2)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 97 percent / water / benzene / 15 h / Heating

3: 65 percent / HOBt, EDC / CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) 0 deg C to RT, 6 h

4: 79 percent / diethylamine / CH₂Cl₂ / 7 h / Ambient temperature

5: 77 percent / HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) 0 deg C to RT, 9 h

With trifluorormethanesulfonic acid; 4 A molecular sieve; water; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; In dichloromethane; benzene;

DOI:10.1021/ja952265x

Reference yield:

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite (153659-02-0) → (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester (178272-03-2)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 97 percent / water / benzene / 15 h / Heating

3: 65 percent / HOBt, EDC / CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) 0 deg C to RT, 6 h

4: 79 percent / diethylamine / CH₂Cl₂ / 7 h / Ambient temperature

5: 77 percent / HOBt, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) 0 deg C to RT, 9 h

With trifluorormethanesulfonic acid; 4 A molecular sieve; water; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; In dichloromethane; benzene;

DOI:10.1021/ja952265x

upstream raw materials:

BOC-L-aspartic acid 4-benzyl ester

(1R,2R)-trans-2-azidocyclohexanol

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite

(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine

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