Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-acetylamino-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-acetylamino-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-trityloxymethyl-tetrahydro-pyran-3-yl ester
• CAS No.: 83032-29-5
• Molecular Formula: C₄₃H₅₁NO₁₃
• Molecular Weight: 789.877

Synonyms:

Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-acetylamino-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-acetylamino-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-trityloxymethyl-tetrahydro-pyran-3-yl ester

There total 8 articles about Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-acetylamino-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-trityloxymethyl-tetrahydro-pyran-3-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:

3-O-(3,4-didesoxy-6-O-trityl-α-D-glycero-hex-3-enopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (61865-88-1) → 3-O-(2-acetamido-3,4-di-O-acetyl-2-desoxy-6-O-trityl-α-D-galactopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (83032-29-5)

Guidance literature:

Multi-step reaction with 4 steps

2: 68 percent / pyridine

3: 46.5 percent / 1 M aluminium hydroxide / H₂O / 3 h / 40 °C

4: pyridine / 16 h / Ambient temperature

With aluminum hydroxide; In pyridine; water;

DOI:10.1016/S0008-6215(00)82219-3

Reference yield:

3-O-(3,4-didesoxy-6-O-trityl-α-D-glycero-hex-3-enopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (61865-88-1) → Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-acetylamino-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-trityloxymethyl-tetrahydro-pyran-3-yl ester (83032-26-2,83032-29-5)

Guidance literature:

Multi-step reaction with 4 steps

2: 68 percent / pyridine

3: 19 percent / 1 M aluminium hydroxide / H₂O / 3 h / 40 °C

4: pyridine

With aluminum hydroxide; In pyridine; water;

DOI:10.1016/S0008-6215(00)82219-3

Reference yield:

(2R,4R,5R,6R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-4,5-dihydroxy-6-trityloxymethyl-dihydro-pyran-3-one oxime (83032-23-9) → 3-O-(2-acetamido-3,4-di-O-acetyl-2-desoxy-6-O-trityl-α-D-galactopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (83032-29-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / pyridine

2: 46.5 percent / 1 M aluminium hydroxide / H₂O / 3 h / 40 °C

3: pyridine / 16 h / Ambient temperature

With aluminum hydroxide; In pyridine; water;

DOI:10.1016/S0008-6215(00)82219-3

upstream raw materials:

acetic anhydride

3-O-(2-Acetamido-2-desoxy-6-O-trityl-α-D-galactopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

3-O-(3,4-didesoxy-6-O-trityl-α-D-glycero-hex-3-enopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

(2R,4R,5R,6R)-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-4,5-dihydroxy-6-trityloxymethyl-dihydro-pyran-3-one oxime

Downstream raw materials:

3-O-(2-acetamido-2-desoxy-α-D-talopyranosyl)-D-glucose

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