benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

Base Information

Chemical Name:benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside
CAS No.:262599-58-6
Molecular Formula:C₆₃H₆₅N₃O₁₄
Molecular Weight:1088.22
Hs Code.:

Synonyms:benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

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Chemical Property of benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

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Technology Process of benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

There total 7 articles about benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-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: 55.0%

: 127873-82-9,127874-09-3,127875-25-6,127875-32-5
4-O-allyl-2,3,6-tri-O-benzyl-D-glycopyranose

: 262599-18-8
benzyl 3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

: 262599-58-6
benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

: benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

Guidance literature:: With silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride; In dichloromethane; at -60 - 0 ℃;
DOI:10.1246/bcsj.73.173

Reference yield:

: 111240-23-4
benzyl 2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

: 262599-58-6
benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / ZnCl₂ / 20 °C

2: 85 percent / sodium hydride / dimethylformamide / 0.5 h / 20 °C

3: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

4: 41 percent / p-nitrobenzenesulfonyl chloride; silver trifluoromethanesulfonate; triethylamine / CH₂Cl₂ / -60 - 0 °C

With triethylsilane; silver trifluoromethanesulfonate; sodium hydride; triethylamine; trifluoroacetic acid; 4-Nitrobenzenesulfonyl chloride; zinc(II) chloride; In dichloromethane; N,N-dimethyl-formamide; 1: acetalization / 2: Alkylation / 3: Reduction / 4: glycosylation;
DOI:10.1246/bcsj.73.173

Reference yield:

: 7784-55-6,10060-23-8
Tetraacetyl-<2,4-dinitrophenyl>-glucosamin

: 262599-58-6
benzyl O-(4-O-allyl-2,3,6-tri-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: AcBr; H₂O / CHCl₃ / 1.55 h / 0 - 20 °C

2: 73 percent / Hg(CN)2; HgBr₂ / acetonitrile / 20 °C

3: 2.93 g / NaOMe / methanol / 2 h / 40 °C

4: 79 percent / ZnCl₂ / 20 °C

5: 85 percent / sodium hydride / dimethylformamide / 0.5 h / 20 °C

6: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 0 °C

7: 41 percent / p-nitrobenzenesulfonyl chloride; silver trifluoromethanesulfonate; triethylamine / CH₂Cl₂ / -60 - 0 °C

With triethylsilane; Acetyl bromide; water; sodium methylate; silver trifluoromethanesulfonate; mercury(II) cyanide; sodium hydride; triethylamine; trifluoroacetic acid; 4-Nitrobenzenesulfonyl chloride; mercury dibromide; zinc(II) chloride; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: glycosylation / 3: Deacetylation / 4: acetalization / 5: Alkylation / 6: Reduction / 7: glycosylation;
DOI:10.1246/bcsj.73.173