2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

Chemical Name:2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
CAS No.:224309-17-5
Molecular Formula:C₃₄H₄₀N₄O₆Si
Molecular Weight:628.8
Hs Code.:

Synonyms:2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

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Chemical Property of 2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

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Technology Process of 2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 3 articles about 2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 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: 68.0%

: 100-39-0
benzyl bromide

: 224309-14-2
2-[(2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

: 224309-17-5
2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1016/S0960-894X(99)00154-7

Reference yield:

: 224309-10-8
2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

: 224309-17-5
2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / imidazole / dimethylformamide / Ambient temperature

2: 68 percent / NaH / dimethylformamide / 0 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(99)00154-7

Reference yield:

: Trifluoro-methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-6-benzyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

: 224309-17-5
2-[(2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 4 steps

1: NaN₃ / dimethylformamide / 75 °C

2: 79 percent / aq. AcOH / 70 °C

3: 87 percent / imidazole / dimethylformamide / Ambient temperature

4: 68 percent / NaH / dimethylformamide / 0 °C

With 1H-imidazole; sodium azide; sodium hydride; acetic acid; In N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(99)00154-7