4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

Chemical Name:4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
CAS No.:717132-51-9
Molecular Formula:C₆₄H₇₀O₁₅S
Molecular Weight:1111.32
Hs Code.:

Synonyms:4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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Chemical Property of 4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

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Technology Process of 4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 8 articles about 4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-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: 71.0%

: 62-50-0
Ethyl methanesulfonate

: 717132-50-8
4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

: {(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-4-yl}-methanesulfonic acid ethyl ester

: 717132-51-9
4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Guidance literature:: Ethyl methanesulfonate; With n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; for 0.25h;

4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1081/CAR-120037571

Reference yield:

: 150412-80-9
4-methoxyphenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

: 717132-51-9
4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 66 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 80 °C

2.1: NaH / dimethylformamide / 2 h / 0 °C

3.1: 13 g / aq. HCl / methanol / 2 h / 50 °C

4.1: Bu₂SnO / methanol / 2 h / Heating

4.2: 88 percent / dimethylformamide / 48 h / 20 °C

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 91 percent / dimethylformamide / 1 h / 0 °C

6.1: 87 percent / p-TsOH / Pd/C / ethyl acetate; ethanol / 2 h / 80 °C

7.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

8.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -60 °C

8.2: 71 percent / hexane; tetrahydrofuran / -78 - 20 °C

With hydrogenchloride; n-butyllithium; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 7.1: Dess-Martin oxidation;
DOI:10.1081/CAR-120037571

Reference yield:

: 717132-42-8
4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-β-D-glucopyranoside

: 717132-51-9
4-methoxyphenyl 2,4,6-tri-O-benzyl-3-C-ethoxysulfonylmethyl-β-D-gulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 13 g / aq. HCl / methanol / 2 h / 50 °C

3.1: Bu₂SnO / methanol / 2 h / Heating

3.2: 88 percent / dimethylformamide / 48 h / 20 °C

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 91 percent / dimethylformamide / 1 h / 0 °C

5.1: 87 percent / p-TsOH / Pd/C / ethyl acetate; ethanol / 2 h / 80 °C

6.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -60 °C

7.2: 71 percent / hexane; tetrahydrofuran / -78 - 20 °C

With hydrogenchloride; n-butyllithium; sodium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 6.1: Dess-Martin oxidation;
DOI:10.1081/CAR-120037571