4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol

Base Information

Chemical Name:4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol
CAS No.:1255526-26-1
Molecular Formula:C₃₇H₄₁N₃O₅
Molecular Weight:607.75
Hs Code.:

Synonyms:4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol

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Chemical Property of 4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol

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Technology Process of 4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol

There total 4 articles about 4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol 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: 89.0%

: 4,8-anhydro-1-bromo-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol

: 1255526-26-1
4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 5h;
DOI:10.1016/j.carres.2017.04.010

Reference yield: 60.0%

: 173829-80-6
3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-propanol

: 1255526-26-1
4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol

Guidance literature:: With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; Inert atmosphere;
DOI:10.1021/ol102310x

Reference yield:

: 80300-30-7
1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

: 1255526-26-1
4,8-anhydro-1-azido-1,2,3-trideoxy-5,6,7,9-tetra-O-benzyl-D-glycero-D-gulo-nonitol

Guidance literature:: Multi-step reaction with 4 steps

1.1: trimethylsilyl iodide / dichloromethane / 1 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / Inert atmosphere; Reflux

2.2: 0 - 20 °C / Inert atmosphere

3.1: triphenylphosphine; carbon tetrabromide / dichloromethane / Inert atmosphere

4.1: sodium azide / N,N-dimethyl-formamide / 5 h / 80 °C

With sodium azide; trimethylsilyl iodide; carbon tetrabromide; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2017.04.010