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

Base Information

Chemical Name: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
CAS No.:188399-09-9
Molecular Formula:C₅₁H₅₂N₄O₁₁
Molecular Weight:896.994
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 10 articles about 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 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: 85.0%

: 188399-08-8
2-[(2R,3R,4R,5S,6R)-4-Allyloxy-2-azido-6-benzyloxymethyl-5-((2S,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-benzyloxymethyl-4-ethoxymethoxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

: 188399-09-9
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

Guidance literature:: With boron trifluoride diethyl etherate; thiophenol; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1016/S0968-0896(96)00209-X

Reference yield:

: 188398-94-9
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

: 188399-09-9
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

Guidance literature:: Multi-step reaction with 7 steps

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

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

3: 79 percent / Ag₂O, Bu₄NI / dimethylformamide / 16 h / 0 °C

4: 96 percent / 60percent aq. AcOH / 2 h / 65 °C

5: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) 1,4-dioxane, 50 deg C, 21 h

6: 67 percent / NaH / dimethylformamide / 2 h / Ambient temperature

7: 85 percent / BF₃*Et₂O, thiophenol / CH₂Cl₂ / 3 h / 0 °C

With methanol; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; thiophenol; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; 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

: 188399-09-9
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

Guidance literature:: Multi-step reaction with 6 steps

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

2: 79 percent / Ag₂O, Bu₄NI / dimethylformamide / 16 h / 0 °C

3: 96 percent / 60percent aq. AcOH / 2 h / 65 °C

4: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) 1,4-dioxane, 50 deg C, 21 h

5: 67 percent / NaH / dimethylformamide / 2 h / Ambient temperature

6: 85 percent / BF₃*Et₂O, thiophenol / CH₂Cl₂ / 3 h / 0 °C

With boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; thiophenol; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0968-0896(96)00209-X