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

Base Information

• Chemical Name: 2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione
• CAS No.: 224309-10-8
• Molecular Formula: C₂₁H₂₀N₄O₆
• Molecular Weight: 424.413

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

Chemical Property of 2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Chemical Property:

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Technology Process of 2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

There total 2 articles about 2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-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: 79.0%

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 (224309-08-4) → 2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (224309-10-8)

Guidance literature:

With acetic acid; at 70 ℃;

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

Guidance literature:

Multi-step reaction with 2 steps

1: NaN₃ / dimethylformamide / 75 °C

2: 79 percent / aq. AcOH / 70 °C

With sodium azide; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00154-7

Reference yield: 87.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2-((2R,3R,4S,5S,6R)-4-Azido-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (224309-10-8) → 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 (224309-14-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0960-894X(99)00154-7

upstream raw materials:

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

Downstream raw materials:

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

((2R,3S,4S,5R,6R)-5-Amino-4-azido-3,6-bis-benzyloxy-tetrahydro-pyran-2-yl)-methanol

((2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

2-((2R,3R,4S,5S,6R)-4-Azido-2,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

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