2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-isoindole-1,3-dione
• CAS No.: 185022-22-4
• Molecular Formula: C₃₇H₃₇NO₈
• Molecular Weight: 623.703

Synonyms:2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-isoindole-1,3-dione

Chemical Property of 2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

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Technology Process of 2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-isoindole-1,3-dione

There total 2 articles about 2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-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: 29.0%

2-(2-hydroxyethoxy)-2,3-dihydro-1H-isoindole-1,3-dione (32380-69-1) + 1-O-acetyl-2,3,4-tri-O-benzyl-β-L-fucopyranose (146815-26-1) → 2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-isoindole-1,3-dione (185022-22-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/0040-4020(96)00870-8

Reference yield:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9) → 2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-isoindole-1,3-dione (185022-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 2 h

2: 29 percent / 4 A molecular sieves, TMSOTf / CH₂Cl₂ / -78 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triethylamine; In dichloromethane;

DOI:10.1016/0040-4020(96)00870-8

Reference yield: 97.0%

2-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethoxy]-isoindole-1,3-dione (185022-22-4) → O-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethyl]-hydroxylamine (185022-10-0)

Guidance literature:

With hydrazine hydrate; In ethanol; dichloromethane; for 1h;

DOI:10.1016/0040-4020(96)00870-8

upstream raw materials:

2-(2-hydroxyethoxy)-2,3-dihydro-1H-isoindole-1,3-dione

1-O-acetyl-2,3,4-tri-O-benzyl-β-L-fucopyranose

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

Downstream raw materials:

O-[2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-ethyl]-hydroxylamine

C₅₅H₆₁N₃O₁₂Si

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