[(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Base Information

Chemical Name:[(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester
CAS No.:866333-33-7
Molecular Formula:C₂₁H₃₃N₃O₆
Molecular Weight:423.51
Hs Code.:

Synonyms:[(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

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Chemical Property of [(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

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Technology Process of [(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

There total 10 articles about [(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl 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%

: 866333-31-5
[(2S,3S,4S,5S,6R)-6-(Acetylamino-methyl)-5-azido-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

: 866333-33-7
[(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: [(2S,3S,4S,5S,6R)-6-(Acetylamino-methyl)-5-azido-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester; With triphenylphosphine; In tetrahydrofuran;

In water; at 60 ℃;
DOI:10.1016/j.tetlet.2005.07.081

Reference yield:

: 866333-09-7
(2R,3S,4S,5S,6S)-5-Azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-ol

: 866333-33-7
[(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 84 percent / Et₃N / CH₂Cl₂

2.1: 81 percent / H₂ / Pd/C / ethanol

3.1: 93 percent / Et₃N / CH₂Cl₂

4.1: 80 percent / NaN₃ / dimethylformamide / 100 °C

5.1: 89 percent / TBAF / tetrahydrofuran

6.1: 79 percent / PPh₃; DEAD / tetrahydrofuran

7.1: 100 percent / NH₂NH₂*H₂O / ethanol

8.1: 100 percent / K₂CO₃ / CH₂Cl₂

9.1: PPh₃ / tetrahydrofuran

9.2: 73 percent / H₂O / 60 °C

With sodium azide; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.07.081

Reference yield:

: 866333-11-1
Methanesulfonic acid (2R,3S,4S,5S,6S)-5-azido-4-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yl ester

: 866333-33-7
[(2S,3S,4R,5S,6R)-6-(Acetylamino-methyl)-5-amino-4-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 81 percent / H₂ / Pd/C / ethanol

2.1: 93 percent / Et₃N / CH₂Cl₂

3.1: 80 percent / NaN₃ / dimethylformamide / 100 °C

4.1: 89 percent / TBAF / tetrahydrofuran

5.1: 79 percent / PPh₃; DEAD / tetrahydrofuran

6.1: 100 percent / NH₂NH₂*H₂O / ethanol

7.1: 100 percent / K₂CO₃ / CH₂Cl₂

8.1: PPh₃ / tetrahydrofuran

8.2: 73 percent / H₂O / 60 °C

With sodium azide; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; hydrazine hydrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.07.081