2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 212198-11-3
• Molecular Formula: C₃₆H₅₅NO₁₄
• Molecular Weight: 725.831

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-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: 73.0%

Benzyl-β-D-N-acetyllactosamine (53167-38-7) + pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester (212198-11-3)

Guidance literature:

With bis(tri-n-butyltin)oxide; In acetonitrile; benzene; at 90 ℃; for 24h;

DOI:10.1080/07328309808002347

Reference yield:

benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside (53167-37-6) → 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester (212198-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 0.5 h / Ambient temperature

2: 73 percent / bis(tributyltin)oxide / acetonitrile; benzene / 24 h / 90 °C

With sodium methylate; bis(tri-n-butyltin)oxide; In methanol; acetonitrile; benzene;

DOI:10.1080/07328309808002347

Reference yield:

2-methyl{3,6-di-O-acetyl-1,2-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyrano}[2,1-d]oxazoline (53167-36-5) → 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester (212198-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 1.5 h

2: NaOMe / methanol / 0.5 h / Ambient temperature

3: 73 percent / bis(tributyltin)oxide / acetonitrile; benzene / 24 h / 90 °C

With sodium methylate; pyridinium p-toluenesulfonate; bis(tri-n-butyltin)oxide; In methanol; 1,2-dichloro-ethane; acetonitrile; benzene;

DOI:10.1080/07328309808002347

upstream raw materials:

Benzyl-β-D-N-acetyllactosamine

pivaloyl chloride

benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside

2-methyl{3,6-di-O-acetyl-1,2-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyrano}[2,1-d]oxazoline

Downstream raw materials:

C₃₉H₅₆Cl₃NO₁₆

C₄₃H₆₀Cl₃NO₁₈

2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-3,5-diacetoxy-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester

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