Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine

Base Information

Chemical Name:Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine
CAS No.:163456-98-2
Molecular Formula:C₃₇H₄₁NO₅
Molecular Weight:579.736
Hs Code.:

Synonyms:Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine

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Chemical Property of Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine

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Technology Process of Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine

There total 1 articles about Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine 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:

: (2S,3S,4R)-2,3,4-Tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde

: 100-46-9
benzylamine

: 163456-98-2
Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine

Guidance literature:: DOI:10.1016/0040-4020(95)00029-8

Reference yield: 86.0%

: 54125-02-9
danishefsky's diene

: 163456-98-2
Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine

: 163456-99-3
N-benzyl-(6S,1'R,2'R,3'R,4'R)-6-(1',2',3'-tri-O-benzyl-4',5'-O-isopropylidene-1',2',3',4',5'-pentahydroxy-1'-pentyl)-2,3-didehydropiperidine-4-one

Guidance literature:: With zinc(II) chloride; In acetonitrile; for 3h;
DOI:10.1016/0040-4020(95)00029-8

Reference yield:

: 163456-98-2
Benzyl-[(2R,3R,4R)-2,3,4-tris-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-(Z)-ylidene]-amine

: (2S,3R,4R)-4-((2S,4R)-1-Benzyl-4-hydroxy-piperidin-2-yl)-2,3,4-tris-benzyloxy-butyraldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / ZnCl₂ / acetonitrile / 3 h

2: 91 percent / NaBH₄ / ethanol / 24 h

3: 81 percent / 85 percent trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

4: Pb(OAc)4 / toluene / 0.5 h

With lead(IV) acetate; sodium tetrahydroborate; trifluoroacetic acid; zinc(II) chloride; In ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1016/0040-4020(95)00029-8