2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 866332-83-4
• Molecular Formula: C₂₁H₃₁NO₇
• Molecular Weight: 409.48
• Mol file: 866332-83-4.mol

Synonyms:2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

There total 4 articles about 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-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: 76.0%

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester (866332-82-3) → 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester (866332-83-4)

Guidance literature:

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 - 20 ℃;

With sodium nitrite; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.07.081

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester (866332-83-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 87 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

3.1: Tf₂O; pyridine / CH₂Cl₂ / 0 - 20 °C

3.2: 76 percent / NaNO₂ / dimethylformamide

With pyridine; triethylsilane; trifluoromethylsulfonic anhydride; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.tetlet.2005.07.081

Reference yield:

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-α-D-glucopyranoside (120489-36-3) → 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester (866332-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0 - 20 °C

2.1: Tf₂O; pyridine / CH₂Cl₂ / 0 - 20 °C

2.2: 76 percent / NaNO₂ / dimethylformamide

With pyridine; triethylsilane; trifluoromethylsulfonic anhydride; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.tetlet.2005.07.081

upstream raw materials:

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6R)-3-acetylamino-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester

pivaloyl chloride

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-α-D-glucopyranoside

N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

Downstream raw materials:

2,2-Dimethyl-propionic acid (2S,3S,4R,5R,6S)-3-azido-2-benzyloxymethyl-5-tert-butoxycarbonylamino-6-methoxy-tetrahydro-pyran-4-yl ester

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-3-acetylamino-5-azido-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-4-yl ester