3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Base Information

Chemical Name:3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol
CAS No.:1268670-62-7
Molecular Formula:C₃₅H₄₃N₃O₄Si
Molecular Weight:597.83
Hs Code.:

Synonyms:3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

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Chemical Property of 3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

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Technology Process of 3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

There total 5 articles about 3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-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:

: 3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-1-C-(t-butyldimethylsilyl)-8-O-tosyl-D-glycero-D-gulo-oct-1-ynitol

: 1268670-62-7
3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 55 ℃; for 16h;
DOI:10.1039/c0cc04127k

Reference yield:

: 1268670-57-0
3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-1-C-(trimethylsilyl)-8-O-(1-trimethylsilyloxyvinyl)-D-glycero-D-gulo-oct-1-ynitol

: 1268670-62-7
3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: tetrahydrofuran / 0.17 h / -30 °C / Alkaline conditions

2.2: 2 h / -30 - -10 °C

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

4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 55 °C

With sodium azide; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; 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

: 1268670-62-7
3,7-anhydro-8-azido-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-(t-butyldimethylsilyl)-D-glycero-D-gulo-oct-1-ynitol

Guidance literature:: Multi-step reaction with 5 steps

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

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

3.1: tetrahydrofuran / 0.17 h / -30 °C / Alkaline conditions

3.2: 2 h / -30 - -10 °C

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

5.1: sodium azide / N,N-dimethyl-formamide / 16 h / 55 °C

With sodium azide; trimethylsilyl trifluoromethanesulfonate; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c0cc04127k