(3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane

Base Information

Chemical Name:(3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane
CAS No.:1366423-02-0
Molecular Formula:C₅₁H₆₃NO₅
Molecular Weight:770.065
Hs Code.:

Synonyms:(3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane

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Chemical Property of (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane

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Technology Process of (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane

There total 10 articles about (3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane 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: 84.0%

: 112-31-2
caprinaldehyde

: 1366422-50-5
(3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)azocane

: 1366423-02-0
(3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane

Guidance literature:: With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/jo202054g

Reference yield:

: 166592-73-0
methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

: 1366423-02-0
(3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane

Guidance literature:: Multi-step reaction with 10 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole; iodine; triphenylphosphine / toluene / 3 h / 70 °C / Inert atmosphere

3.1: zinc / tetrahydrofuran; water / 2 h / 40 °C / Sonication

4.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux

7.1: water; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III) / tetrahydrofuran; tert-butyl alcohol / 0.08 h / 0 °C / Inert atmosphere

7.2: K₂OsO₂(OH)4 / 40 h / 20 °C / Inert atmosphere

8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

9.1: naphthalene; sodium / 1,2-dimethoxyethane / 0.5 h / -78 °C / Inert atmosphere

10.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; naphthalene; tetrabutyl ammonium fluoride; water; iodine; sodium; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); zinc; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol; 7.1: Sharpless cis-asymmetric dihydroxylation / 7.2: Sharpless cis-asymmetric dihydroxylation;
DOI:10.1021/jo202054g

Reference yield:

: 359714-89-9
(2S,3S,4R)-N-allyl-2,3,4-tris(benzyloxy)hex-5-en-1-amine

: 1366423-02-0
(3S,4R,5S,6R,7R)-3,4,5,6,7-pentakis(benzyloxy)-1-nonylazocane

Guidance literature:: Multi-step reaction with 6 steps

1.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux

3.1: water; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III) / tetrahydrofuran; tert-butyl alcohol / 0.08 h / 0 °C / Inert atmosphere

3.2: K₂OsO₂(OH)4 / 40 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

5.1: naphthalene; sodium / 1,2-dimethoxyethane / 0.5 h / -78 °C / Inert atmosphere

6.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; naphthalene; water; sodium; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol; 3.1: Sharpless cis-asymmetric dihydroxylation / 3.2: Sharpless cis-asymmetric dihydroxylation;
DOI:10.1021/jo202054g