2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 187938-33-6
• Molecular Formula: C₃₇H₄₅NO₁₅
• Molecular Weight: 743.762

Synonyms:2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 4 articles about 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl 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: 66.0%

2,2-Dimethyl-propionic acid (3aS,4R,6S,7R,7aS)-7-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (187938-33-6)

Guidance literature:

With acetic acid; at 65 ℃; for 2.5h;

DOI:10.1039/a605439k

Reference yield:

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (187938-33-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / MeONa, MeOH / CH₂Cl₂ / 2 h / 0 °C

2: 89 percent / p-TSA / 1.5 h / Ambient temperature

3: 89 percent / pyridine / 12 h / Ambient temperature

4: 66 percent / 70percent aq. AcOH / 2.5 h / 65 °C

With pyridine; methanol; sodium methylate; toluene-4-sulfonic acid; acetic acid; In dichloromethane;

DOI:10.1039/a605439k

Reference yield:

2,2-Dimethyl-propionic acid (3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yloxy]-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-[(2R,3S,4R,5R,6R)-4-acetoxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-tetrahydro-pyran-3-yloxy]-3,4-dihydroxy-tetrahydro-pyran-2-ylmethyl ester (187938-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / pyridine / 12 h / Ambient temperature

2: 66 percent / 70percent aq. AcOH / 2.5 h / 65 °C

With pyridine; acetic acid;

DOI:10.1039/a605439k

Downstream raw materials:

C₇₇H₉₀N₂O₃₁

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