benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside
CAS No.:124814-06-8
Molecular Formula:C₆₁H₆₄O₁₁
Molecular Weight:973.173
Hs Code.:

Synonyms:benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

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Chemical Property of benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

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Technology Process of benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

There total 15 articles about benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside 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: 62.0%

: 124814-05-7
benzyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-α-D-glucopyranoside

: 124814-06-8
benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

Guidance literature:: With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h;
DOI:10.1016/0008-6215(89)84070-4

Reference yield:

: 97590-76-6
benzyl-O-β-D-glucopyranoside

: 124814-06-8
benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: NaOAc / 4 h / 110 °C

2: 69.3 percent / 1.) crushed molecular sieves (4 Angstroem); 2.) trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1.) r.t., 0.5 h; 2.) -20 deg C to r.t.

3: 1percent NaOMe / methanol / Ambient temperature

4: ZnCl₂ / Ambient temperature

5: NaH (60percent dispersion in oil) / dimethylformamide / -30 °C

6: toluene / Heating

7: 95 percent / Na / methanol; dioxane / Ambient temperature

8: 94 percent / NaH (60percent dispersion in oil) / dimethylformamide / 1 h / Ambient temperature

9: 62 percent / sodium cyanoborohydride, HCl, crushed molecular sieves (4 Angstroem) / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; sodium acetate; sodium; sodium hydride; sodium cyanoborohydride; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(89)84070-4

Reference yield:

: 100-39-0
benzyl bromide

: 124814-06-8
benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) NaH (60percent dispersion in oil); 2.) 60percent aq. acetic acid; 3.) 0.1M H₂SO₄ / 1.) DMF, 90 deg C, 2 h; 2.) 90 deg C, 2 h; 3.) 90 deg C, 2 h

2: NaOAc / 4 h / 110 °C

3: 69.3 percent / 1.) crushed molecular sieves (4 Angstroem); 2.) trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1.) r.t., 0.5 h; 2.) -20 deg C to r.t.

4: 1percent NaOMe / methanol / Ambient temperature

5: ZnCl₂ / Ambient temperature

6: NaH (60percent dispersion in oil) / dimethylformamide / -30 °C

7: toluene / Heating

8: 95 percent / Na / methanol; dioxane / Ambient temperature

9: 94 percent / NaH (60percent dispersion in oil) / dimethylformamide / 1 h / Ambient temperature

10: 62 percent / sodium cyanoborohydride, HCl, crushed molecular sieves (4 Angstroem) / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; sodium methylate; sodium acetate; sodium; sodium hydride; sodium cyanoborohydride; acetic acid; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/0008-6215(89)84070-4