(S)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester
• CAS No.: 208192-90-9
• Molecular Formula: C₂₈H₃₃F₃N₂O₁₄
• Molecular Weight: 678.57

Synonyms:

Chemical Property of (S)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester

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Technology Process of (S)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester

There total 3 articles about (S)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic 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: 27.0%

2-Benzyloxycarbonylamino-2-trifluoromethyl-succinic acid 1-methyl ester (129398-30-7) + dicyclohexyl-carbodiimide (538-75-0) → 2-Benzyloxycarbonylamino-4-(1,3-dicyclohexyl-ureido)-4-oxo-2-trifluoromethyl-butyric acid methyl ester + (S)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester (208192-90-9) + (R)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester

Guidance literature:

With 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine; In dichloromethane; Yields of byproduct given;

DOI:10.1055/s-1998-4491

Reference yield: 11.0%

2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine (41355-50-4,51642-81-0,58484-22-3,70128-27-7,70145-20-9,94482-21-0,98300-76-6) + 2-Benzyloxy-6-oxo-4-trifluoromethyl-5,6-dihydro-4H-[1,3]oxazine-4-carboxylic acid methyl ester (139741-42-7) → (S)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester (208192-90-9) + (R)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester

Guidance literature:

at 100 ℃; for 12h;

DOI:10.1055/s-1998-4491

Reference yield:

2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine (41355-50-4,51642-81-0,58484-22-3,70128-27-7,70145-20-9,94482-21-0,98300-76-6) + 2-Benzyloxycarbonylamino-2-trifluoromethyl-succinic acid 1-methyl ester (129398-30-7) → 2-Benzyloxycarbonylamino-4-(1,3-dicyclohexyl-ureido)-4-oxo-2-trifluoromethyl-butyric acid methyl ester + (S)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester (208192-90-9) + (R)-2-Benzyloxycarbonylamino-N-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-2-trifluoromethyl-succinamic acid methyl ester

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1055/s-1998-4491

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine

2-Benzyloxy-6-oxo-4-trifluoromethyl-5,6-dihydro-4H-[1,3]oxazine-4-carboxylic acid methyl ester

2-Benzyloxycarbonylamino-2-trifluoromethyl-succinic acid 1-methyl ester

dicyclohexyl-carbodiimide

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