Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
CAS No.:309913-20-0
Molecular Formula:C₅₅H₅₅ClO₁₁S
Molecular Weight:959.554
Hs Code.:

Synonyms:Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

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Chemical Property of Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

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Technology Process of Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

There total 5 articles about Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-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: 90.0%

: 79-04-9
chloroacetyl chloride

: 259742-19-3
phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-1^I-thio-β-maltoside

: 309913-20-0
Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: With dmap; In dichloromethane; at -10 - -7 ℃; for 0.25h;
DOI:10.1055/s-2000-7601

Reference yield:

: 87470-75-5
phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

: 309913-20-0
Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / imidazole / dimethylformamide / 0.75 h / 15 - 20 °C

2: 56 percent / aq. NaOH; Bu₄NHSO₄ / toluene / 72 h / 20 °C

3: 95 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

4: 90 percent / DMAP / CH₂Cl₂ / 0.25 h / -10 - -7 °C

With 1H-imidazole; dmap; sodium hydroxide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Etherification / 3: Silyl ether cleavage / 4: Esterification;
DOI:10.1055/s-2000-7601

Reference yield:

: 309913-14-2
Phenyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glycopyranosyl)-1-thio-β-D-glucopyranoside

: 309913-20-0
Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / NaOMe; MeOH / 1 h / 20 °C

2: 85 percent / imidazole / dimethylformamide / 0.75 h / 15 - 20 °C

3: 56 percent / aq. NaOH; Bu₄NHSO₄ / toluene / 72 h / 20 °C

4: 95 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

5: 90 percent / DMAP / CH₂Cl₂ / 0.25 h / -10 - -7 °C

With 1H-imidazole; methanol; dmap; sodium hydroxide; tetrabutyl ammonium fluoride; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Deacetylation / 2: Etherification / 3: Etherification / 4: Silyl ether cleavage / 5: Esterification;
DOI:10.1055/s-2000-7601