4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:296769-08-9
Molecular Formula:C₅₄H₅₀ClNO₁₀S
Molecular Weight:940.511
Hs Code.:

Synonyms:4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of 4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of 4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 4 articles about 4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-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: 48.0%

: 4-chlorophenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside

: 296768-93-9
4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 296769-08-9
4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: 4-chlorophenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside; With diphenylchlorosulfonium chloride; In dichloromethane; at -78 - 20 ℃; for 1.5h;

4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside; With calcium sulfate; silver trifluoromethanesulfonate; silver carbonate; In hexane; dichloromethane; at -78 ℃; for 0.5h; Further stages.;
DOI:10.1021/ol0063050

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 296769-08-9
4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 73 percent / BF₃*Et₂O / CH₂Cl₂

2.1: NaOMe / methanol; CH₂Cl₂

2.2: 63 percent / p-TsOH / dimethylformamide

3.1: Ph₂SCl⁽¹⁺⁾*Cl^(1-) / CH₂Cl₂ / 1.5 h / -78 - 20 °C

3.2: 48 percent / Drierite; silver carbonate; silver trifluoromethanesulfonate / CH₂Cl₂; hexane / 0.5 h / -78 °C

With boron trifluoride diethyl etherate; sodium methylate; diphenylchlorosulfonium chloride; In methanol; dichloromethane; 1.1: Substitution / 2.1: Deacetylation / 2.2: benzylidenation / 3.1: Substitution / 3.2: glycosidation;
DOI:10.1021/ol0063050

Reference yield:

: 106-54-7
p-Chlorothiophenol

: 296769-08-9
4-chlorophenyl 3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 73 percent / BF₃*Et₂O / CH₂Cl₂

2.1: NaOMe / methanol; CH₂Cl₂

2.2: 63 percent / p-TsOH / dimethylformamide

3.1: Ph₂SCl⁽¹⁺⁾*Cl^(1-) / CH₂Cl₂ / 1.5 h / -78 - 20 °C

3.2: 48 percent / Drierite; silver carbonate; silver trifluoromethanesulfonate / CH₂Cl₂; hexane / 0.5 h / -78 °C

With boron trifluoride diethyl etherate; sodium methylate; diphenylchlorosulfonium chloride; In methanol; dichloromethane; 1.1: Substitution / 2.1: Deacetylation / 2.2: benzylidenation / 3.1: Substitution / 3.2: glycosidation;
DOI:10.1021/ol0063050