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

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2S,3S,4R,5R,6S)-3-azido-2-benzyloxymethyl-5-tert-butoxycarbonylamino-6-methoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 866332-85-6
• Molecular Formula: C₂₄H₃₆N₄O₇
• Molecular Weight: 492.572
• Mol file: 866332-85-6.mol

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

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

There total 7 articles about 2,2-Dimethyl-propionic acid (2S,3S,4R,5R,6S)-3-azido-2-benzyloxymethyl-5-tert-butoxycarbonylamino-6-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: 85.0%

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-3-acetylamino-5-azido-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-4-yl ester (866332-84-5) + di-tert-butyl dicarbonate (24424-99-5) → 2,2-Dimethyl-propionic acid (2S,3S,4R,5R,6S)-3-azido-2-benzyloxymethyl-5-tert-butoxycarbonylamino-6-methoxy-tetrahydro-pyran-4-yl ester (866332-85-6)

Guidance literature:

2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-3-acetylamino-5-azido-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-4-yl ester; di-tert-butyl dicarbonate; With dmap; In tetrahydrofuran; Heating;

With H₄N₂*HO^(1-); In tetrahydrofuran; methanol;

DOI:10.1016/j.tetlet.2005.07.081

Reference yield:

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,3S,4R,5R,6S)-3-azido-2-benzyloxymethyl-5-tert-butoxycarbonylamino-6-methoxy-tetrahydro-pyran-4-yl ester (866332-85-6)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: 76 percent / NaNO₂ / dimethylformamide

2.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

3.1: sodium azide / dimethylformamide / 110 °C

4.1: DMAP / tetrahydrofuran / Heating

4.2: 85 percent / NH₂NH₂*xH₂O / methanol; tetrahydrofuran

With pyridine; dmap; sodium azide; trifluoromethylsulfonic anhydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.07.081

Reference yield:

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) → 2,2-Dimethyl-propionic acid (2S,3S,4R,5R,6S)-3-azido-2-benzyloxymethyl-5-tert-butoxycarbonylamino-6-methoxy-tetrahydro-pyran-4-yl ester (866332-85-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: sodium azide / dimethylformamide / 110 °C

3.1: DMAP / tetrahydrofuran / Heating

3.2: 85 percent / NH₂NH₂*xH₂O / methanol; tetrahydrofuran

With dmap; sodium azide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.07.081

upstream raw materials:

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

di-tert-butyl dicarbonate

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

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