methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

Base Information

Chemical Name:methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside
CAS No.:213768-14-0
Molecular Formula:C₄₈H₆₀O₁₁
Molecular Weight:812.998
Hs Code.:

Synonyms:methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

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Chemical Property of methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

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Technology Process of methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

There total 21 articles about methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside 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:

: 100-39-0
benzyl bromide

: 213768-14-0
methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 84 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) o deg C to room temperature

2: 84 percent / 80percent AcOH / 4 h / 80 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1.) MeOH, reflux, 2.5 h, 2.) toluene, 60 deg C, 15 h

4: 84 percent / pyridine / Ambient temperature

5: 84 percent / TBAF / tetrahydrofuran / 6 h / Ambient temperature

6: 88 percent / pyridine / Ambient temperature

7: 95 percent / Na / methanol

8: 77 percent / NIS, TfOH / CH₂Cl₂ / Ambient temperature

9: 85 percent / p-toluenesulfonic acid / methanol; ethyl acetate / 6 h

10: 34 percent / NaH, Cs₂CO₃ / tetrahydrofuran / 24 h / Heating

11: 1.) t-BuOK, 2.) HgO, HgCl₂ / 1.) DMSO, 80 deg C, 2 h, 2.) acetone, H₂O, 30 min

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; caesium carbonate; toluene-4-sulfonic acid; acetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo9806097

Reference yield:

: 629-30-1
1,7-heptandiol

: 213768-14-0
methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 57 percent / pyridine; CH₂Cl₂ / Ambient temperature

2: 78 percent / pyridine; CH₂Cl₂ / Ambient temperature

3: 91 percent / NaH / tetrahydrofuran / 1.) 50 deg C, 1 h, 2.) 65 deg C, 18 h

4: 77 percent / NIS, TfOH / CH₂Cl₂ / Ambient temperature

5: 85 percent / p-toluenesulfonic acid / methanol; ethyl acetate / 6 h

6: 34 percent / NaH, Cs₂CO₃ / tetrahydrofuran / 24 h / Heating

7: 1.) t-BuOK, 2.) HgO, HgCl₂ / 1.) DMSO, 80 deg C, 2 h, 2.) acetone, H₂O, 30 min

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium tert-butylate; sodium hydride; caesium carbonate; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo9806097

Reference yield:

: 131089-35-5
methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside

: 213768-14-0
methyl 2-O-(2',3',4'-tri-O-benzyl-α-D-galactopyranosyl)-4-O-benzyl-6,6'-di-O-(heptane-1,7-diyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 84 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) o deg C to room temperature

2: 84 percent / 80percent AcOH / 4 h / 80 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1.) MeOH, reflux, 2.5 h, 2.) toluene, 60 deg C, 15 h

4: 84 percent / pyridine / Ambient temperature

5: 84 percent / TBAF / tetrahydrofuran / 6 h / Ambient temperature

6: 88 percent / pyridine / Ambient temperature

7: 95 percent / Na / methanol

8: 77 percent / NIS, TfOH / CH₂Cl₂ / Ambient temperature

9: 85 percent / p-toluenesulfonic acid / methanol; ethyl acetate / 6 h

10: 34 percent / NaH, Cs₂CO₃ / tetrahydrofuran / 24 h / Heating

11: 1.) t-BuOK, 2.) HgO, HgCl₂ / 1.) DMSO, 80 deg C, 2 h, 2.) acetone, H₂O, 30 min

With N-iodo-succinimide; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; caesium carbonate; toluene-4-sulfonic acid; acetic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo9806097