Acetic acid (2R,3R,4R,5S,6S)-2-((S)-2-{(R)-2-[(2R,3R)-2-((R)-2-acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyrylamino]-propionylamino}-propoxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5S,6S)-2-((S)-2-{(R)-2-[(2R,3R)-2-((R)-2-acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyrylamino]-propionylamino}-propoxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 138588-08-6
• Molecular Formula: C₃₁H₄₈N₄O₁₁
• Molecular Weight: 652.742

Synonyms:

Chemical Property of Acetic acid (2R,3R,4R,5S,6S)-2-((S)-2-{(R)-2-[(2R,3R)-2-((R)-2-acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyrylamino]-propionylamino}-propoxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4R,5S,6S)-2-((S)-2-{(R)-2-[(2R,3R)-2-((R)-2-acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyrylamino]-propionylamino}-propoxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester

There total 9 articles about Acetic acid (2R,3R,4R,5S,6S)-2-((S)-2-{(R)-2-[(2R,3R)-2-((R)-2-acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyrylamino]-propionylamino}-propoxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl 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: 43.0%

(2R,3R)-2-((R)-2-Acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid (138588-07-5) + Acetic acid (2R,3R,4R,5S,6S)-2-[(S)-2-((R)-2-amino-propionylamino)-propoxy]-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester (138588-04-2) → Acetic acid (2R,3R,4R,5S,6S)-2-((S)-2-{(R)-2-[(2R,3R)-2-((R)-2-acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyrylamino]-propionylamino}-propoxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester (138588-08-6)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In acetonitrile; for 18h; Ambient temperature;

DOI:10.1016/0040-4039(91)80238-2

Reference yield:

methyl 3,4-di-O-methyl-α-L-rhamnopyranoside (35939-76-5) → Acetic acid (2R,3R,4R,5S,6S)-2-((S)-2-{(R)-2-[(2R,3R)-2-((R)-2-acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyrylamino]-propionylamino}-propoxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester (138588-08-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 3N H₂SO₄ / dioxane / 6 h / 100 °C

2: DMAP, pyridine / 18 h / Ambient temperature

3: HBr, AcOH / CH₂Cl₂ / 3 h / 0 °C

4: 81 percent / HgBr₂, Hg(CN)2 / CH₂Cl₂ / 18 h / Ambient temperature

5: H₂ / 10percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature

6: DCC, HOBt / CH₂Cl₂ / 18 h / Ambient temperature

7: H₂ / 10percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature

8: 43 percent / DCC, HOBt / acetonitrile / 18 h / Ambient temperature

With pyridine; dmap; sulfuric acid; hydrogen bromide; hydrogen; mercury(II) cyanide; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; mercury dibromide; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; acetonitrile;

DOI:10.1016/0040-4039(91)80238-2

Reference yield:

O3,O4-dimethyl-α-L-6-deoxy-mannopyranose (25672-82-6) → Acetic acid (2R,3R,4R,5S,6S)-2-((S)-2-{(R)-2-[(2R,3R)-2-((R)-2-acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyrylamino]-propionylamino}-propoxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester (138588-08-6)

Guidance literature:

Multi-step reaction with 7 steps

1: DMAP, pyridine / 18 h / Ambient temperature

2: HBr, AcOH / CH₂Cl₂ / 3 h / 0 °C

3: 81 percent / HgBr₂, Hg(CN)2 / CH₂Cl₂ / 18 h / Ambient temperature

4: H₂ / 10percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature

5: DCC, HOBt / CH₂Cl₂ / 18 h / Ambient temperature

6: H₂ / 10percent Pd/C / methanol / 1 h / 760 Torr / Ambient temperature

7: 43 percent / DCC, HOBt / acetonitrile / 18 h / Ambient temperature

With pyridine; dmap; hydrogen bromide; hydrogen; mercury(II) cyanide; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; mercury dibromide; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/0040-4039(91)80238-2

upstream raw materials:

(2R,3R)-2-((R)-2-Acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid

Acetic acid (2R,3R,4R,5S,6S)-2-[(S)-2-((R)-2-amino-propionylamino)-propoxy]-4,5-dimethoxy-6-methyl-tetrahydro-pyran-3-yl ester

methyl 3,4-di-O-methyl-α-L-rhamnopyranoside

O³,O⁴-dimethyl-α-L-6-deoxy-mannopyranose

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