(3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine

Base Information

Chemical Name:(3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine
CAS No.:180196-26-3
Molecular Formula:C₃₆H₄₈ClNO₄Si
Molecular Weight:622.32
Hs Code.:

Synonyms:(3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine

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Chemical Property of (3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine

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Technology Process of (3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine

There total 6 articles about (3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine 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:

: 180196-28-5
(2R,3R,4S,6R)-1-Azido-2,3,4-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-9-chloro-nonan-5-one

: 180196-26-3
(3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine

Guidance literature:: With hydrogen; palladium dihydroxide; In ethanol; ethyl acetate; for 1h;
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

: 180196-26-3
(3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine

Guidance literature:: Multi-step reaction with 6 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

5: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 10 min, 2.) CH₂Cl₂, -60 deg C, 15 min

6: H₂ / Pd(OH)2/C / ethanol; ethyl acetate / 1 h

With 1H-imidazole; osmium(VIII) oxide; hydrogen azide; oxalyl dichloride; hydrogen; potassium hexamethylsilazane; sodium hydrogensulfite; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; ethanol; ethyl acetate; 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

: 180196-26-3
(3R,4R,5R)-3,4,5-Tris-benzyloxy-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-4-chloro-butyl]-2,3,4,5-tetrahydro-pyridine

Guidance literature:: Multi-step reaction with 5 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

4: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 10 min, 2.) CH₂Cl₂, -60 deg C, 15 min

5: H₂ / Pd(OH)2/C / ethanol; ethyl acetate / 1 h

With 1H-imidazole; osmium(VIII) oxide; hydrogen azide; oxalyl dichloride; hydrogen; sodium hydrogensulfite; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; In tetrahydrofuran; ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo960609b