(1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine

Base Information

Chemical Name:(1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine
CAS No.:1319731-11-7
Molecular Formula:C₃₅H₃₉NO₄
Molecular Weight:537.699
Hs Code.:

Synonyms:(1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine

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Chemical Property of (1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine

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Technology Process of (1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine

There total 10 articles about (1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine 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: 93.0%

: 1319731-24-2
(1S,2S,3S,4S,6R)-4-azido-6-benzyloxymethyl-1,2,3-tris(benzyloxy)cyclohexane

: 1319731-11-7
(1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 25 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ja202610x

Reference yield:

: 869476-26-6
2,3-di-O-benzyl-2,3-dihydroxypent-4-enal

: 1319731-11-7
(1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine; di-n-butylboron trifluoromethanesulphonate / dichloromethane / -78 - 0 °C / Inert atmosphere

1.2: 3 h / -78 - 15 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran; diethyl ether; water / 0 - 20 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 40 °C / Darkness; Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 °C / Inert atmosphere

4.2: 6 h / 20 °C / Inert atmosphere

5.1: borane-THF / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5.2: 0 - 25 °C / Inert atmosphere

6.1: triethylamine / 0 - 25 °C / Inert atmosphere

7.1: sodium azide / N,N-dimethyl-formamide / 90 °C / Inert atmosphere

8.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; lithium borohydride; sodium azide; borane-THF; sodium hydride; triethylamine; di-n-butylboron trifluoromethanesulphonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ja202610x

Reference yield:

: 924298-42-0
(1R,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanol

: 1319731-11-7
(1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)cyclohexanamine

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / 0 - 25 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 90 °C / Inert atmosphere

3: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

With lithium aluminium tetrahydride; sodium azide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja202610x