(S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid
• CAS No.: 196098-21-2
• Molecular Formula: C₂₅H₃₂N₂O₁₃
• Molecular Weight: 568.535

Synonyms:(S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid

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Technology Process of (S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid

There total 1 articles about (S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid 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: 49.0%

N-(benzyloxycarbonyl)-L-serine (1145-80-8) + 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → (S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid (196098-21-2)

Guidance literature:

With MS 4 Angstroem; boron trifluoride diethyl etherate; In dichloromethane; for 120h; Ambient temperature;

DOI:10.1021/ja971383c

Reference yield: 88.0%

(S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid (196098-21-2) + C14H23N2O2(1+)*BrH*Br(1-) → N-Benzyloxycarbonyl-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-phenylalanine choline ester bromide

Guidance literature:

With benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1250::AID-ANIE1250>3.0.CO;2-M

Reference yield: 81.0%

(S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-propionic acid (196098-21-2) + C11H25N2O2(1+)*BrH*Br(1-) → N-Benzyloxycarbonyl-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-leucine choline ester bromide

Guidance literature:

With benzotriazol-1-ol; diisopropyl-carbodiimide; In dichloromethane;

DOI:10.1002/(SICI)1521-3773(19990503)38:9<1250::AID-ANIE1250>3.0.CO;2-M

upstream raw materials:

N-(benzyloxycarbonyl)-L-serine

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

Downstream raw materials:

N-Benzyloxycarbonyl-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-leucine

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