2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Base Information

Chemical Name:2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione
CAS No.:210645-10-6
Molecular Formula:C₃₅H₃₂BrNO₆
Molecular Weight:642.546
Hs Code.:

Synonyms:2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

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Chemical Property of 2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

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Technology Process of 2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

There total 7 articles about 2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-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:

: 168644-99-3
ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 210645-10-6
2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Guidance literature:: With bromine; In dichloromethane; at 0 ℃; for 0.75h;
DOI:10.1135/cccc19980577

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 210645-10-6
2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 72 percent / 4 Angstroem molecular sieves, TiCl₄ / CH₂Cl₂ / 1 h / Ambient temperature

2: 90 percent / CH₃ONa / methanol / 1.) r.t., 2 h, 2.) 3 deg C, overnight

3: 72 percent / NaH / dimethylformamide / Ambient temperature

4: Br₂ / CH₂Cl₂ / 0.75 h / 0 °C

With 4 A molecular sieve; bromine; sodium methylate; titanium tetrachloride; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1135/cccc19980577

Reference yield:

: 31505-46-1
tetra-O-acetyl-2-(2-carboxy-benzoylamino)-2-deoxy-β-D-glucopyranose

: 210645-10-6
2-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 4-DMAP, Ac₂O / CH₂Cl₂

2: 72 percent / 4 Angstroem molecular sieves, TiCl₄ / CH₂Cl₂ / 1 h / Ambient temperature

3: 90 percent / CH₃ONa / methanol / 1.) r.t., 2 h, 2.) 3 deg C, overnight

4: 72 percent / NaH / dimethylformamide / Ambient temperature

5: Br₂ / CH₂Cl₂ / 0.75 h / 0 °C

With dmap; 4 A molecular sieve; bromine; sodium methylate; acetic anhydride; titanium tetrachloride; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1135/cccc19980577