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

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Chemical Name: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
CAS No.:224309-14-2
Molecular Formula:C₂₇H₃₄N₄O₆Si
Molecular Weight:538.676
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 3 articles about 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 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: 87.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

: 224309-14-2
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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1016/S0960-894X(99)00154-7

Reference yield:

: 224309-08-4
2-((2R,4aR,6R,7R,8S,8aS)-8-Azido-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 79 percent / aq. AcOH / 70 °C

2: 87 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; acetic acid; 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

: 224309-14-2
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

Guidance literature:: Multi-step reaction with 3 steps

1: NaN₃ / dimethylformamide / 75 °C

2: 79 percent / aq. AcOH / 70 °C

3: 87 percent / imidazole / dimethylformamide / Ambient temperature

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