ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside
CAS No.:370554-23-7
Molecular Formula:C₆₅H₆₃Cl₂NO₁₂S
Molecular Weight:1153.19
Hs Code.:

Synonyms:ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

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Chemical Property of ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

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Technology Process of ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

There total 16 articles about ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-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: 94.0%

: 370554-21-5
3,4,6-tri-O-benzyl-2-O-p-toluoyl-β-D-galactopyranosyl fluoride

: 370554-17-9
ethyl 3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

: 370554-23-7
ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; at -20 ℃; for 1h;
DOI:10.1246/cl.2001.840

Reference yield: 84.0%

: 370554-17-9
ethyl 3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

: 370554-19-1
phenyl 3,4,6-tri-O-benzyl-2-O-p-toluoyl-β-D-galactopyranosyl carbonate

: 370554-23-7
ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

Guidance literature:: With trityl tetrakis(pentafluorophenyl)borate; In various solvent(s); at -15 ℃; for 5h;
DOI:10.1246/cl.2001.840

Reference yield:

: 3254-15-7
3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose

: 370554-23-7
ethyl 3,6-di-O-benzyl-4-O-(3',4',6'-tri-O-benzyl-2'-O-p-toluoyl-β-D-galactopyranosyl)-2-deoxy-2-(4,5-dichlorophthalimido)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: MeONa / methanol / 3 h / 20 °C

2.1: NaH / dimethylformamide; various solvent(s) / 6.5 h / 20 °C

3.1: HCl; silica gel / H₂O; CH₂Cl₂ / 3 h / 20 °C

3.2: NaOMe / methanol / 3 h / 20 °C

4.1: pyridine; 4-dimethylaminopyridine / 4 h / 0 °C

4.2: 2,6-lutidine / 2 h / 20 °C

5.1: Et₂O*BF₃ / CH₂Cl₂ / 0 - 20 °C

6.1: nBu₄NIO₄; TfOH / H₂O; acetonitrile / 3 h / 0 °C

7.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

8.1: 84 percent / Ph₃CB(C₆F₅)4 / molecular sieves 5 Angstroem / various solvent(s) / 5 h / -15 °C

With pyridine; hydrogenchloride; dmap; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; sodium methylate; silica gel; sodium hydride; tetrabutylammonium periodite; triethylamine; trityl tetrakis(pentafluorophenyl)borate; 5A molecular sieve; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1246/bcsj.76.1829