(R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester
• CAS No.: 430474-94-5
• Molecular Formula: C₃₁H₃₄N₂O₉
• Molecular Weight: 578.619
• Mol file: 430474-94-5.mol

Synonyms:(R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

Chemical Property of (R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

There total 5 articles about (R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic 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: 68.0%

benzyl 2-carbobenzyloxyamino-2-deoxy-α-D-galactopyranosiduronic acid (114612-09-8) + D-phenylalanine methyl ester (21685-51-8) → (R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester (430474-94-5)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.7164/antibiotics.55.191

Reference yield:

benzyl 2-carbobenzyloxyamino-2-deoxy-α-D-galactopyranoside (4713-66-0) → (R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester (430474-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / O₂; NaHCO₃ / Pt / H₂O / 5 h / 80 °C

2: 68 percent / 1-hydroxybenzotriazole; ethyldiisopropylamine; 1,3-dicyclohexylcarbodiimide / dimethylformamide / 18 h / 20 °C

With oxygen; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; platinum; In water; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.55.191

Reference yield:

2-carbobenzyloxyamino-2-deoxy-D-galactopyranose (3006-58-4) → (R)-2-[((2S,3R,4R,5R,6S)-6-Benzyloxy-5-benzyloxycarbonylamino-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester (430474-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / acetyl chloride / 1.5 h / 80 °C

2: 97 percent / O₂; NaHCO₃ / Pt / H₂O / 5 h / 80 °C

3: 68 percent / 1-hydroxybenzotriazole; ethyldiisopropylamine; 1,3-dicyclohexylcarbodiimide / dimethylformamide / 18 h / 20 °C

With oxygen; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; acetyl chloride; dicyclohexyl-carbodiimide; platinum; In water; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.55.191

upstream raw materials:

benzyl 2-carbobenzyloxyamino-2-deoxy-α-D-galactopyranosiduronic acid

D-phenylalanine methyl ester

benzyl 2-carbobenzyloxyamino-2-deoxy-α-D-galactopyranoside

2-carbobenzyloxyamino-2-deoxy-D-galactopyranose

Downstream raw materials:

(R)-2-{[(2S,3R,4R,5R,6S)-6-Benzyloxy-5-((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-3-phenyl-propionic acid methyl ester