(S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide

Base Information

• Chemical Name: (S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide
• CAS No.: 208579-97-9
• Molecular Formula: C₁₉H₂₉NO₇
• Molecular Weight: 383.442
• Mol file: 208579-97-9.mol

Synonyms:(S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide

Chemical Property of (S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide

There total 1 articles about (S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide 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: 73.0%

(3S)-3-hydroxydihydrofuran-2(3H)-one (52079-23-9) + methyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside (178812-81-2) → (S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide (208579-97-9)

Guidance literature:

With pyridine; at 100 ℃;

DOI:10.1080/07328309808002896

Reference yield: 95.0%

benzoyl chloride (98-88-4) + (S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide (208579-97-9) → methyl 3-O-benzyl-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycerotetronamido)-2-O-methyl-α-D-mannopyranoside (208579-98-0)

Guidance literature:

With pyridine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1080/07328309808002896

Reference yield:

(S)-N-((2R,3R,4S,5S,6S)-4-Benzyloxy-5,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl)-2,4-dihydroxy-butyramide (208579-97-9) → methyl 3,4,6-trideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside (208580-01-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 100 percent / H₂ / Pd/C / methanol

3: 91 percent / toluene / 6 h / Heating

4: 92 percent / 2,2'-azobis(2-methylpropionitrile), Bu₃SnH / toluene / 0.17 h / 110 °C

With pyridine; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; palladium on activated charcoal; In methanol; dichloromethane; toluene;

DOI:10.1080/07328309808002896

upstream raw materials:

(3S)-3-hydroxydihydrofuran-2(3H)-one

methyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside

Downstream raw materials:

methyl 3-O-benzyl-4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycerotetronamido)-2-O-methyl-α-D-mannopyranoside

methyl 3,4,6-trideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside

methyl 4,6-dideoxy-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-2-O-methyl-α-D-mannopyranoside

methyl 3-O-imidazoylthiocarbonyl-4-(2,4-di-O-benzoyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside