(R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-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-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester
• CAS No.: 624737-91-3
• Molecular Formula: C₃₄H₅₄N₄O₁₁
• Molecular Weight: 694.823
• Mol file: 624737-91-3.mol

Synonyms:

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

There total 5 articles about (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-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:

octyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside (147126-58-7,383417-49-0) → (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester (624737-91-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / TsOH / 1 h

2: 92 percent / sodium hydride / dioxane / 1 h / 65 °C

3: dicyclohexylcarbodiimide

4: triethylamine / pH 8

5: 0.72 g / acetic acid / H₂O / Heating

With sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; water;

DOI:10.1023/A:1023944818406

Reference yield:

n-octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (173725-22-9) → (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester (624737-91-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / sodium methanolate / methanol

2: 84 percent / TsOH / 1 h

3: 92 percent / sodium hydride / dioxane / 1 h / 65 °C

4: dicyclohexylcarbodiimide

5: triethylamine / pH 8

6: 0.72 g / acetic acid / H₂O / Heating

With sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; methanol; water; 1: Zemplen deacetylation;

DOI:10.1023/A:1023944818406

Reference yield:

octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (500767-96-4) → (R)-4-{(S)-2-[(R)-2-((2R,3R,4R,5S,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-2-octyloxy-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester (624737-91-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / sodium hydride / dioxane / 1 h / 65 °C

2: dicyclohexylcarbodiimide

3: triethylamine / pH 8

4: 0.72 g / acetic acid / H₂O / Heating

With sodium hydride; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; water;

DOI:10.1023/A:1023944818406

upstream raw materials:

octyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside

n-octyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-β-D-glucopyranoside