(2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-amine

Base Information

• Chemical Name: (2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-amine
• CAS No.: 909801-45-2
• Molecular Formula: C₃₁H₃₇NO₃
• Molecular Weight: 471.64
• Mol file: 909801-45-2.mol

Synonyms:(2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-amine

Chemical Property of (2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-amine

There total 7 articles about (2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-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: 48.0%

1-bromo-4-butene (5162-44-7) + 2-[(2R,3R,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-yl]isoindoline-1,3-dione (203112-67-8) → (2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-amine (909801-45-2)

Guidance literature:

2-[(2R,3R,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-yl]isoindoline-1,3-dione; With methylamine; In water; at 50 ℃; for 1.5h;

With potassium carbonate; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h;

1-bromo-4-butene; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1055/s-0035-1562438

Reference yield:

3-butene-1-amine (2524-49-4) + (3S,4R)-1,3,4-tris(benzyloxy)-hex-5-en-2-one (220939-94-6) → (2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-amine (909801-45-2) + (2S,3R,4R)-1,3,4-tris(benzyloxy)-2-(but-3-enylamino)-hex-5-ene

Guidance literature:

With indium(III) chloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1039/b605818c

Reference yield:

methyl 1,3,4-tri-O-benzyl-6-deoxy-6-iodo-D-fructofuranoside → (2R,3R,4R)-1,3,4-Tris(benzyloxy)-N-(but-3-en-1-yl)hex-5-en-2-amine (909801-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / zinc / H₂O; tetrahydrofuran / 2 h / 40 °C / sonication

2: 3 Angstroem molecular sieves; InCl₃; NaCNBH₃ / tetrahydrofuran / 3 h / 20 °C

With indium(III) chloride; 3 A molecular sieve; sodium cyanoborohydride; zinc; In tetrahydrofuran; water;

DOI:10.1039/b605818c

upstream raw materials:

3-butene-1-amine

(3S,4R)-1,3,4-tris(benzyloxy)-hex-5-en-2-one

(3R,4R,5S)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

L-xylose

Downstream raw materials:

(2R,3R,4R)-N-trifluoroacetyl-1,3,4-tris(benzyloxy)-2-(but-3-enylamino)-hex-5-ene

(2R,3R,4R)-N-benzyloxycarbonyl-1,3,4-tris(benzyloxy)-2-(but-3-enylamino)-hex-5-ene

(1R,2R,3R,7S,7aR)-1,2-dibenzyloxy-3-benzyloxymethyl-7-hydroxy-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine