5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol

Base Information

Chemical Name:5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol
CAS No.:616215-38-4
Molecular Formula:C₅₀H₅₅N₃O₅Si
Molecular Weight:806.089
Hs Code.:

Synonyms:5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol

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Chemical Property of 5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol

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Technology Process of 5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol

There total 4 articles about 5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol 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: 75.2%

: 616215-36-2
(3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(tert-butyldiphenylsilyloxy)hexan-2-ol

: 616215-38-4
5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol

Guidance literature:: With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1002/ejoc.201100452

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 616215-38-4
5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol

Guidance literature:: Multi-step reaction with 3 steps

1: sodium tetrahydroborate / ethanol; dichloromethane / 48 h

2: 1H-imidazole / dichloromethane / 1 h / Inert atmosphere

3: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1002/ejoc.201100452

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 616215-38-4
5-azido-2,3,4,6-tetra-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-L-iditol

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / Inert atmosphere

2: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201200923