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

Base Information

• Chemical Name: octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-β-D-glucopyranoside
• CAS No.: 500767-97-5
• Molecular Formula: C₂₂H₃₉NO₈
• Molecular Weight: 445.554

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

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

Chemical Property:

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

There total 1 articles about octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-β-D-glucopyranoside 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: 92.0%

(S)-2-bromopropanoic acid (32644-15-8,10327-08-9) + octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside (500767-96-4) → octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-β-D-glucopyranoside (500767-97-5)

Guidance literature:

With sodium hydride; In 1,4-dioxane; at 65 ℃; for 1h;

DOI:10.1023/A:1023944818406

Reference yield:

octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-β-D-glucopyranoside (500767-97-5) → (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 3 steps

1: dicyclohexylcarbodiimide

2: triethylamine / pH 8

3: 0.72 g / acetic acid / H₂O / Heating

With acetic acid; triethylamine; dicyclohexyl-carbodiimide; In water;

DOI:10.1023/A:1023944818406

Reference yield:

octyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-β-D-glucopyranoside (500767-97-5) → (R)-4-{(S)-2-[(R)-2-((4aR,6R,7R,8R,8aS)-7-Acetylamino-2,2-dimethyl-6-octyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester (500767-98-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylcarbodiimide

2: triethylamine / pH 8

With triethylamine; dicyclohexyl-carbodiimide;

DOI:10.1023/A:1023944818406

upstream raw materials:

(S)-2-bromopropanoic acid

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

Downstream raw materials:

(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

(R)-4-{(S)-2-[(R)-2-((4aR,6R,7R,8R,8aS)-7-Acetylamino-2,2-dimethyl-6-octyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester

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