2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 188399-01-1
• Molecular Formula: C₃₃H₃₈N₄O₁₁
• Molecular Weight: 666.685
• Mol file: 188399-01-1.mol

Synonyms:2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property of 2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 5 articles about 2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-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: 67.0%

2-{(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-[(3aS,4R,6S,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione (188399-03-3) → 2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (188399-01-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1016/S0968-0896(96)00209-X

Reference yield:

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (188398-94-9) → 2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (188399-01-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe, MeOH / CH₂Cl₂ / 4 h / Ambient temperature

2: p-toluenesulfonic acid monohydrate / acetone / 2 h / Heating

With methanol; sodium methylate; toluene-4-sulfonic acid; In dichloromethane; acetone;

DOI:10.1016/S0968-0896(96)00209-X

Reference yield:

2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione → 2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (188399-01-1)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 3 h / Ambient temperature

2: 75 percent / p-toluenesulfonic acid monohydrate / acetone / 4 h / Ambient temperature

3: 67 percent / Bu₄NF / tetrahydrofuran / 24 h / Ambient temperature

With 1H-imidazole; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0968-0896(96)00209-X

upstream raw materials:

2,2-dimethoxy-propane

2-{(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-[(3aS,4R,6S,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

2-{(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-[(2S,3R,4S,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

Downstream raw materials:

2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,5-bis-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-5-((2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-4-ethoxymethoxy-5-hydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione