(2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol
CAS No.:180196-25-2
Molecular Formula:C₃₆H₅₀ClN₃O₅Si
Molecular Weight:668.349
Hs Code.:

Synonyms:(2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol

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Chemical Property of (2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol

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Technology Process of (2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol

There total 4 articles about (2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol 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: 88.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 180196-24-1
(4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

: 180196-25-2
(2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol

Guidance literature:: With 1H-imidazole; In tetrahydrofuran; N,N-dimethyl-formamide; for 20h; Ambient temperature;
DOI:10.1021/jo960609b

Reference yield:

: 18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1
2,3,4-tri-O-benzyl-D-arabinopyranose

: 180196-25-2
(2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) potassium bis(trimethylsilil)amide / 1.) THF, toluene, 0 deg C, 30 min, 2.) THF, -78 -> 0 deg C, 6 h

2: 84 percent / hydrazoic acid, PPh₃, diethyl azodicarboxylate / benzene / 0.42 h / Ambient temperature

3: 1.) 4percent OsO₄, N-methylmorfoline N-oxide, 2.) 10percent sodium bisulfite / 1.) THF, t-BuOH, H₂O, 72 h, 2.) 30 min

4: 88 percent / imidazole / tetrahydrofuran; dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; osmium(VIII) oxide; hydrogen azide; potassium hexamethylsilazane; sodium hydrogensulfite; 4-methylmorpholine N-oxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo960609b

Reference yield:

: 154813-30-6
(Z)-(2R,3S,4R)-2,3,4-tris(benzyloxy)-9-chloro-5-nonen-1-ol

: 180196-25-2
(2R,3R,4R,5S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / hydrazoic acid, PPh₃, diethyl azodicarboxylate / benzene / 0.42 h / Ambient temperature

2: 1.) 4percent OsO₄, N-methylmorfoline N-oxide, 2.) 10percent sodium bisulfite / 1.) THF, t-BuOH, H₂O, 72 h, 2.) 30 min

3: 88 percent / imidazole / tetrahydrofuran; dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; osmium(VIII) oxide; hydrogen azide; sodium hydrogensulfite; 4-methylmorpholine N-oxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo960609b