methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

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Chemical Name:methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside
CAS No.:114284-22-9
Molecular Formula:C₂₃H₃₄O₁₁
Molecular Weight:486.516
Hs Code.:

Synonyms:methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

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Chemical Property of methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

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Technology Process of methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

There total 8 articles about methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside 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: 94.0%

: 114284-21-8
methyl 2-O-benzyl-6-O-tert-butyldiphenylsilyl-3-O-(6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

: 114284-22-9
methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;
DOI:10.1016/0008-6215(87)80098-8

Reference yield:

: 15038-71-8,15384-58-4,23392-29-2,40653-23-4,57539-07-8,76375-66-1,81872-62-0,86363-45-3,90639-38-6,108739-91-9,116002-34-7,130192-76-6,131433-04-0,141115-75-5,78185-83-8
methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside

: 114284-22-9
methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 1) Hg(CN)2, molecular sieves / 1) nitromethane, reflux, 3 h; 2) nitromethane, 40-45 deg C, 3 h

2: 60 percent / sodium methoxide / methanol / 4 h / Ambient temperature

3: 92 percent / acetic acid / H₂O / 2 h / 90 °C

4: 74.4 percent / imidazole / dimethylformamide / 1 h / 0 °C

5: 84.3 percent / p-toluenesulfonic acid monohydrate / acetone / 1 h / Ambient temperature

6: 1) molecular sieves, pyridinium chlorocromate; 2) NaBH₄ / 1) dichloromethane, room temp., 24 h; 2) aq. ethanol, 0 deg C, 1 h

7: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0008-6215(87)80098-8

Reference yield:

: 114284-13-8,136657-64-2
methyl 2-O-benzyl-4,6-O-benzylidene-3-O-α-D-mannopyranosyl-α-D-mannopyranoside

: 114284-22-9
methyl 2-O-benzyl-3-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / acetic acid / H₂O / 2 h / 90 °C

2: 74.4 percent / imidazole / dimethylformamide / 1 h / 0 °C

3: 84.3 percent / p-toluenesulfonic acid monohydrate / acetone / 1 h / Ambient temperature

4: 1) molecular sieves, pyridinium chlorocromate; 2) NaBH₄ / 1) dichloromethane, room temp., 24 h; 2) aq. ethanol, 0 deg C, 1 h

5: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

With 1H-imidazole; sodium tetrahydroborate; molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0008-6215(87)80098-8