Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester
• CAS No.: 205750-54-5
• Molecular Formula: C₃₃H₃₆N₂O₁₃
• Molecular Weight: 668.654

Synonyms:

Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

There total 3 articles about Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-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: 92.0%

4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (205750-48-7) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (205750-54-5)

Guidance literature:

With pyridine; hydrogen sulfide; triethylamine; Ambient temperature;

DOI:10.1080/07328309808002324

Reference yield:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (55682-57-0) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (205750-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / N-iodosuccinimide, CF₃SO₂H, molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 92 percent / H₂S, Py/Et₃N / Ambient temperature

With pyridine; N-iodo-succinimide; molecular sieve; trifluoromethanesulfinic acid; hydrogen sulfide; triethylamine; In dichloromethane;

DOI:10.1080/07328309808002324

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-49-7) → Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-4-amino-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester (205750-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / N-iodosuccinimide, CF₃SO₂H, molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 92 percent / H₂S, Py/Et₃N / Ambient temperature

With pyridine; N-iodo-succinimide; molecular sieve; trifluoromethanesulfinic acid; hydrogen sulfide; triethylamine; In dichloromethane;

DOI:10.1080/07328309808002324

upstream raw materials:

4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((1R,2S,3R,4R,5R)-3-benzyloxy-4-tetradecanoylamino-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Tetradecanoic acid [(2R,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-hydroxymethyl-2-tetradecyloxy-tetrahydro-pyran-3-yl]-amide

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-6-((2R,3S,4R,5R,6R)-6-acetoxy-2-acetoxymethyl-4-benzyloxy-5-tetradecanoylamino-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4R,5R,6R)-2-acetoxymethyl-4-benzyloxy-5-tetradecanoylamino-6-tetradecyloxy-tetrahydro-pyran-3-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

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