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

Base Information

• Chemical Name: 2-{(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl}-isoindole-1,3-dione
• CAS No.: 129090-90-0
• Molecular Formula: C₄₆H₅₁NO₁₃
• Molecular Weight: 825.91

Synonyms:

Chemical Property of 2-{(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-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)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl}-isoindole-1,3-dione

There total 10 articles about 2-{(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-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:

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside (76101-14-9) → 2-{(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl}-isoindole-1,3-dione (129090-90-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 4-toluenesulfonic acid / acetonitrile / 12 h / Ambient temperature

2: 1.) sodium hydride / 1.) N,N-dimethylformamide, 15 min, 0 deg C 2.) 1 h, 0 deg C; 3 h, r.t.

3: 70 percent / NaBH₃CN, 3 Angstroem molecular sieves, HCl / tetrahydrofuran; diethyl ether / 5 h / Ambient temperature

4: 72 percent / 4 Angstroem molecular sieves, trimethylsilyl triflate / CH₂Cl₂ / 1 h, -20 deg C; 3 h, r.t.

5: sodium methoxide, methanol / 2 h / Ambient temperature

6: 1.) tributyltin oxide, 4 Angstroem molecular sieves 2.) N-methylimidazole / 1.) acetonitrile, 20 h, reflux 2.) 96 h, reflux

7: 83 percent / 4-toluenesulfonic acid / acetonitrile / 0.08 h / Ambient temperature

8: 1.) NaBH₃CN, 3 Angstroem molecular sieves 2.) trifluoroacetic acid / 1.) oxolane, 30 min, r.t. 2.) 48 h, r.t.

With 1-methyl-1H-imidazole; hydrogenchloride; methanol; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tributyltin oxide; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(90)84225-J

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride (7772-87-4) → 2-{(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl}-isoindole-1,3-dione (129090-90-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) HgO, HgCl₂, Drierite / 1.) dichloromethane, 1 h, r.t. 2.) 48 h

2: sodium methoxide, methanol / dioxane / 1 h / Ambient temperature

3: 4-toluenesulfonic acid / acetonitrile / 12 h / Ambient temperature

4: 1.) sodium hydride / 1.) N,N-dimethylformamide, 15 min, 0 deg C 2.) 1 h, 0 deg C; 3 h, r.t.

5: 70 percent / NaBH₃CN, 3 Angstroem molecular sieves, HCl / tetrahydrofuran; diethyl ether / 5 h / Ambient temperature

6: 72 percent / 4 Angstroem molecular sieves, trimethylsilyl triflate / CH₂Cl₂ / 1 h, -20 deg C; 3 h, r.t.

7: sodium methoxide, methanol / 2 h / Ambient temperature

8: 1.) tributyltin oxide, 4 Angstroem molecular sieves 2.) N-methylimidazole / 1.) acetonitrile, 20 h, reflux 2.) 96 h, reflux

9: 83 percent / 4-toluenesulfonic acid / acetonitrile / 0.08 h / Ambient temperature

10: 1.) NaBH₃CN, 3 Angstroem molecular sieves 2.) trifluoroacetic acid / 1.) oxolane, 30 min, r.t. 2.) 48 h, r.t.

With 1-methyl-1H-imidazole; hydrogenchloride; methanol; calcium sulfate; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tributyltin oxide; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(90)84225-J

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97276-95-4) → 2-{(2R,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yloxy]-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl}-isoindole-1,3-dione (129090-90-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) sodium hydride / 1.) N,N-dimethylformamide, 15 min, 0 deg C 2.) 1 h, 0 deg C; 3 h, r.t.

2: 70 percent / NaBH₃CN, 3 Angstroem molecular sieves, HCl / tetrahydrofuran; diethyl ether / 5 h / Ambient temperature

3: 72 percent / 4 Angstroem molecular sieves, trimethylsilyl triflate / CH₂Cl₂ / 1 h, -20 deg C; 3 h, r.t.

4: sodium methoxide, methanol / 2 h / Ambient temperature

5: 1.) tributyltin oxide, 4 Angstroem molecular sieves 2.) N-methylimidazole / 1.) acetonitrile, 20 h, reflux 2.) 96 h, reflux

6: 83 percent / 4-toluenesulfonic acid / acetonitrile / 0.08 h / Ambient temperature

7: 1.) NaBH₃CN, 3 Angstroem molecular sieves 2.) trifluoroacetic acid / 1.) oxolane, 30 min, r.t. 2.) 48 h, r.t.

With 1-methyl-1H-imidazole; hydrogenchloride; methanol; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tributyltin oxide; sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(90)84225-J

upstream raw materials:

methyl 4-O-<3-O-allyl-4,6-O-(4-methoxybenzylidene)-β-D-galactopyranosyl>-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

methyl 4,6-O-benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

Downstream raw materials:

C₄₈H₄₉F₆NO₁₇S₂

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