2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 419549-78-3
• Molecular Formula: C₅₅H₅₄BrNO₁₀
• Molecular Weight: 968.938

Synonyms:2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property of 2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 11 articles about 2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-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:

ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-75-0) → 2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (419549-78-3)

Guidance literature:

With bromine; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4) → 2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (419549-78-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / NaH / tetrahydrofuran

2: 85 percent / BH₃*Me₃N; 4 Angstroem molecular sieves; AlCl₃ / tetrahydrofuran / 6 h / 20 °C

3: pyridine / CH₂Cl₂ / 2 h / 0 °C

4: 1.08 g / CH₂Cl₂; dimethylformamide / 5 h / 0 °C

5: 73 percent / K₂CO₃ / methanol; tetrahydrofuran / 4 h

6: 82 percent / Ag₂O; KI; 4 Angstroem molecular sieves / dimethylformamide / 5 h / 0 °C

7: 72 percent / (Ph₃P)3RhCl / ethanol / 3 h / Heating

8: 87 mg / tetrabutylammonium bromide; 4 Angstroem molecular sieves / CH₂Cl₂; dimethylformamide / 72 h

9: Br₂ / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; tetrabutylammomium bromide; bromine; sodium hydride; potassium carbonate; potassium iodide; silver(l) oxide; Wilkinson's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-63-6) → 2-[(2R,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-bromo-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (419549-78-3)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 1.08 g / CH₂Cl₂; dimethylformamide / 5 h / 0 °C

3: 73 percent / K₂CO₃ / methanol; tetrahydrofuran / 4 h

4: 82 percent / Ag₂O; KI; 4 Angstroem molecular sieves / dimethylformamide / 5 h / 0 °C

5: 72 percent / (Ph₃P)3RhCl / ethanol / 3 h / Heating

6: 87 mg / tetrabutylammonium bromide; 4 Angstroem molecular sieves / CH₂Cl₂; dimethylformamide / 72 h

7: Br₂ / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; 4 A molecular sieve; tetrabutylammomium bromide; bromine; potassium carbonate; potassium iodide; silver(l) oxide; Wilkinson's catalyst; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

upstream raw materials:

ethyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

perbenzyl fucosyl bromide

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

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