2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol

Base Information Edit

Chemical Name:2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol
CAS No.:634610-83-6
Molecular Formula:C₂₉H₃₃NO₆S
Molecular Weight:523.65
Hs Code.:
Mol file:634610-83-6.mol

Synonyms:2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol

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Chemical Property of 2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol Edit

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Technology Process of 2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol

There total 8 articles about 2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol 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: 83.0%

: 2512-24-5
N-tert-butylbenzenesulfonamide

: 634610-81-4
2-O-benzyl-5-O-(4'-iodophenyl)-1,4:3,6-dianhydro-D-mannitole

: 634610-83-6
2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol

Guidance literature:: N-tert-butylbenzenesulfonamide; With n-butyllithium; In tetrahydrofuran; hexane; for 2h;

With zinc(II) chloride; In tetrahydrofuran; hexane; for 1h;

2-O-benzyl-5-O-(4'-iodophenyl)-1,4:3,6-dianhydro-D-mannitole; With triphenylphosphine; lithium chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; hexane; for 70h; Heating;
DOI:10.1055/s-2003-41426

Reference yield: 58.0%

: 150691-04-6
2-(tert-butylamino)sulfonylphenylboronic acid

: 634610-81-4
2-O-benzyl-5-O-(4'-iodophenyl)-1,4:3,6-dianhydro-D-mannitole

: 634610-83-6
2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol

Guidance literature:: With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; Heating;
DOI:10.1055/s-2003-41426

Reference yield:

: 183624-93-3
(3R,3aR,6R,6aR)-6-benzyloxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

: 634610-83-6
2-O-benzyl-5-O-[4'-(2''-tert-butylamino-sulfonylphenyl)-phenyl]-1,4:3,6-dianhydro-D-mannitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 1 h / 60 °C

1.2: 92 percent / dimethylformamide / 60 °C

2.1: H₂ / Pd/C / methanol; tetrahydrofuran / 0.5 h / 750.06 Torr

3.1: 4.46 g / KNO₂; KI; aq. HBr / dimethylsulfoxide / 0.5 h / 50 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 0 °C

4.2: ZnCl₂ / tetrahydrofuran; hexane / 1 h / 20 °C

4.3: 83 percent / PPh₃; LiCl / Pd₂(dba)3 / tetrahydrofuran; hexane / 70 h / Heating

With n-butyllithium; potassium nitrite; hydrogen bromide; hydrogen; sodium hydride; potassium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.3: Negishi coupling;