Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-carboxy-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-carboxy-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-yl ester
• CAS No.: 81629-60-9
• Molecular Formula: C₅₅H₈₀N₂O₁₇
• Molecular Weight: 1041.24

Synonyms:

Chemical Property of Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-carboxy-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-carboxy-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-yl ester

There total 10 articles about Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-carboxy-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-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:

benzyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O--α-D-glucopyranoside (79957-36-1,81629-37-0) → Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-carboxy-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-yl ester (81629-60-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / hydrogen / 10percent Pd/C / methanol; H₂O; acetic acid / 6.5 h / 30 - 35 °C

2: acetyl chloride / 1,2-dichloro-ethane / 22 h / Ambient temperature

3: acetic acid / 1 h / Ambient temperature

4: 94 percent / ferric chloride / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 84 percent / toluene-p-sulfonic acid monohydrate / 1,2-dichloro-ethane / 30 h / 50 - 60 °C

6: 96 percent / pyridine / 4 h / Ambient temperature

7: 1.) 0.1 M potassium hydroxide, 2.) Amberlite IR-120 (H+) / 1.) 1,4-dioxane, 5 min., room temp.

With pyridine; potassium hydroxide; Amberlite IR-120 (H+); hydrogen; iron(III) chloride; toluene-4-sulfonic acid; acetyl chloride; palladium on activated charcoal; In methanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(00)81038-1

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-carboxy-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-yl ester (81629-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) pyridine, 2.) 70percent aqueous acetic acid / 1.) 1 h., room temp., 2.) 40-45 deg C, 1 h.

2: 84 percent / toluene-p-sulfonic acid monohydrate / 1,2-dichloro-ethane / 30 h / 50 - 60 °C

3: 96 percent / pyridine / 4 h / Ambient temperature

4: 1.) 0.1 M potassium hydroxide, 2.) Amberlite IR-120 (H+) / 1.) 1,4-dioxane, 5 min., room temp.

With pyridine; potassium hydroxide; Amberlite IR-120 (H+); toluene-4-sulfonic acid; acetic acid; In 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(00)81038-1

Reference yield:

2-methyl-<4,6-di-O-acetyl-1,2-dideoxy-3-O--α-D-glucopyrano>-<2,1-d>-2-oxazoline (47483-72-7) → Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-carboxy-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-yl ester (81629-60-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / toluene-p-sulfonic acid monohydrate / 1,2-dichloro-ethane / 30 h / 50 - 60 °C

2: 96 percent / pyridine / 4 h / Ambient temperature

3: 1.) 0.1 M potassium hydroxide, 2.) Amberlite IR-120 (H+) / 1.) 1,4-dioxane, 5 min., room temp.

With pyridine; potassium hydroxide; Amberlite IR-120 (H+); toluene-4-sulfonic acid; In 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(00)81038-1

upstream raw materials:

Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-acetylamino-4-((S)-1-methoxycarbonyl-ethoxy)-tetrahydro-pyran-2-yloxymethyl]-6-benzyloxy-5-octadecanoylamino-tetrahydro-pyran-4-yl ester

benzoyl chloride

2-methyl-<4,6-di-O-acetyl-1,2-dideoxy-3-O--α-D-glucopyrano>-<2,1-d>-2-oxazoline

(S)-2-((2R,3S,4R,5R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yloxy)-propionic acid methyl ester

Downstream raw materials:

benzyl 6-O-<2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-4-O-acetyl-3-O-benzoyl-2-deoxy-2-octadecanoylamino-β-D-glucopyranoside

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