3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol

Base Information

Chemical Name:3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol
CAS No.:1268670-68-3
Molecular Formula:C₆₅H₆₅N₃O₁₁S
Molecular Weight:1096.31
Hs Code.:

Synonyms:3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol

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Chemical Property of 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol

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Technology Process of 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol

There total 7 articles about 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol 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: 74.0%

: 1268670-63-8
3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol

: 1268670-68-3
3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 16h;
DOI:10.1039/c0cc04127k

Reference yield:

: 1268670-59-2
3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-gulo-oct-1-ynitol

: 1268670-68-3
3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 14 h / 20 °C

2: copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 80 °C / Microwave irradiation

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C

With copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c0cc04127k

Reference yield:

: 4356-77-8,35094-65-6,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8,59433-13-5
1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

: 1268670-68-3
3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-8-[4-(2',3',4'-tri-O-benzyl-6'-O-tosyl-α-D-glucopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: Multi-step reaction with 5 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 20 °C

2: sodium hydroxide / methanol; dichloromethane / 1 h / 20 °C

3: triethylamine / dichloromethane / 14 h / 20 °C

4: copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 80 °C / Microwave irradiation

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C

With copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c0cc04127k