2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide

Base Information

Chemical Name:2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide
CAS No.:545400-35-9
Molecular Formula:C₄₇H₇₁N₃O₁₀Si
Molecular Weight:866.18
Hs Code.:

Synonyms:2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide

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Chemical Property of 2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide

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Technology Process of 2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide

There total 8 articles about 2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide 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: 85.0%

: 3282-30-2
pivaloyl chloride

: 545400-08-6
6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide

: 545400-35-9
2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide

Guidance literature:: With pyridine; at 60 ℃;
DOI:10.1002/anie.200390208

Reference yield:

: 629-11-8
1,6-hexanediol

: 545400-35-9
2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide

Guidance literature:: Multi-step reaction with 6 steps

1.1: 88 percent / imidazole / dimethylformamide / 36 h / 20 °C

2.1: 97 percent / tetrabromomethane; triphenylphosphine / CH₂Cl₂ / 15 h / 0 - 20 °C

3.1: LDA / tetrahydrofuran; hexane / 2 h / -20 - 50 °C

3.2: 78 percent / tetrahydrofuran; hexane / 1 h / 40 °C

4.1: oxalyl chloride / CH₂Cl₂ / 20 °C

5.1: 15.90 g / pyridine; DMAP / 20 h / 70 °C

6.1: 85 percent / pyridine / 144 h / 60 °C

With pyridine; 1H-imidazole; dmap; oxalyl dichloride; carbon tetrabromide; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200400253

Reference yield:

: 121671-77-0
6-{[tert-butyl(diphenyl)silyl]oxy}hexan-1-ol

: 545400-35-9
2,3,4-tri-O-pivaloyl-6-O-[2,2-dimethyl-8-(tert-butyldiphenylsilyloxy)-octanoyl]-β-D-galactopyranosyl azide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / tetrabromomethane; triphenylphosphine / CH₂Cl₂ / 15 h / 0 - 20 °C

2.1: LDA / tetrahydrofuran; hexane / 2 h / -20 - 50 °C

2.2: 78 percent / tetrahydrofuran; hexane / 1 h / 40 °C

3.1: oxalyl chloride / CH₂Cl₂ / 20 °C

4.1: 15.90 g / pyridine; DMAP / 20 h / 70 °C

5.1: 85 percent / pyridine / 144 h / 60 °C

With pyridine; dmap; oxalyl dichloride; carbon tetrabromide; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/chem.200400253