(R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester

Base Information

• Chemical Name: (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester
• CAS No.: 172986-19-5
• Molecular Formula: C₃₀H₄₆N₄O₁₁
• Molecular Weight: 638.715

Synonyms:

Chemical Property of (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester

There total 15 articles about (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl 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:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester (172986-19-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 53 percent / acetyl chloride / 4 h / 75 °C

2.1: 58 percent / 10 percent H₂SO₄ / methanol / 0.05 h / 100 °C

3.1: Na / dioxane / 1 h / 90 - 95 °C

3.2: dioxane / 3 h / 60 - 65 °C

4.1: ethanol; diethyl ether

5.1: 60 percent AcOH / Heating

6.1: pyridine

7.1: 850 mg / glac. AcOH; HCl; H₂ / palladium black / dioxane

8.1: thionyl chloride / CHCl₃ / 8 h

9.1: 756 mg / mercury cyanide / CHCl₃ / 12 h

10.1: MeONa / methanol / pH 9

11.1: HCl / acetonitrile; dioxane / Heating

12.1: 5 percent aq. KOH / ethanol / 2 h

13.1: DCC / CHCl₃

14.1: 333 mg / N-methylmorpholine / CHCl₃

15.1: 60 percent AcOH / 0.08 h / 100 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; potassium hydroxide; thionyl chloride; sulfuric acid; hydrogen; sodium methylate; sodium; mercury(II) cyanide; acetic acid; acetyl chloride; dicyclohexyl-carbodiimide; palladium; In 1,4-dioxane; methanol; diethyl ether; ethanol; chloroform; acetonitrile; 1.1: Substitution / 2.1: benzylidenation / 3.1: deprotonation / 3.2: Alkylation / 4.1: Esterification / 5.1: Hydrolysis / 6.1: Acetylation / 7.1: Hydrogenolysis / 8.1: Chlorination / 9.1: Substitution / 10.1: Deacetylation / 11.1: isopropylidenation / 12.1: Hydrolysis / 13.1: Condensation / 14.1: Condensation / 15.1: Hydrolysis;

Reference yield:

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside (2862-03-5) → (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester (172986-19-5)

Guidance literature:

Multi-step reaction with 12 steps

1: ethanol; diethyl ether

2: 60 percent AcOH / Heating

3: pyridine

4: 850 mg / glac. AcOH; HCl; H₂ / palladium black / dioxane

5: thionyl chloride / CHCl₃ / 8 h

6: 756 mg / mercury cyanide / CHCl₃ / 12 h

7: MeONa / methanol / pH 9

8: HCl / acetonitrile; dioxane / Heating

9: 5 percent aq. KOH / ethanol / 2 h

10: DCC / CHCl₃

11: 333 mg / N-methylmorpholine / CHCl₃

12: 60 percent AcOH / 0.08 h / 100 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; potassium hydroxide; thionyl chloride; hydrogen; sodium methylate; mercury(II) cyanide; acetic acid; dicyclohexyl-carbodiimide; palladium; In 1,4-dioxane; methanol; diethyl ether; ethanol; chloroform; acetonitrile; 1: Esterification / 2: Hydrolysis / 3: Acetylation / 4: Hydrogenolysis / 5: Chlorination / 6: Substitution / 7: Deacetylation / 8: isopropylidenation / 9: Hydrolysis / 10: Condensation / 11: Condensation / 12: Hydrolysis;

Reference yield:

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0) → (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-2-butoxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester (172986-19-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Na / dioxane / 1 h / 90 - 95 °C

1.2: dioxane / 3 h / 60 - 65 °C

2.1: ethanol; diethyl ether

3.1: 60 percent AcOH / Heating

4.1: pyridine

5.1: 850 mg / glac. AcOH; HCl; H₂ / palladium black / dioxane

6.1: thionyl chloride / CHCl₃ / 8 h

7.1: 756 mg / mercury cyanide / CHCl₃ / 12 h

8.1: MeONa / methanol / pH 9

9.1: HCl / acetonitrile; dioxane / Heating

10.1: 5 percent aq. KOH / ethanol / 2 h

11.1: DCC / CHCl₃

12.1: 333 mg / N-methylmorpholine / CHCl₃

13.1: 60 percent AcOH / 0.08 h / 100 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; potassium hydroxide; thionyl chloride; hydrogen; sodium methylate; sodium; mercury(II) cyanide; acetic acid; dicyclohexyl-carbodiimide; palladium; In 1,4-dioxane; methanol; diethyl ether; ethanol; chloroform; acetonitrile; 1.1: deprotonation / 1.2: Alkylation / 2.1: Esterification / 3.1: Hydrolysis / 4.1: Acetylation / 5.1: Hydrogenolysis / 6.1: Chlorination / 7.1: Substitution / 8.1: Deacetylation / 9.1: isopropylidenation / 10.1: Hydrolysis / 11.1: Condensation / 12.1: Condensation / 13.1: Hydrolysis;

upstream raw materials:

N-{2-O-[butyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl]-D-lactoyl}-L-alanyl-D-isoglutamine benzyl ester

N-Acetyl-D-glucosamine

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside

benzyl 2-acetamido-2-deoxy-3-O-<(R)-1-(methoxycarbonyl)ethyl>-α-D-glucopyranoside

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