(2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine

Base Information

• Chemical Name: (2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine
• CAS No.: 1354826-74-6
• Molecular Formula: C₃₇H₄₀N₄O₃
• Molecular Weight: 588.75
• Mol file: 1354826-74-6.mol

Synonyms:(2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine

Chemical Property of (2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine

There total 12 articles about (2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine 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: 74.0%

(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)piperidine (1354826-65-5) → (2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine (1354826-74-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

DOI:10.1021/acs.orglett.0c00503

Reference yield: 52.0%

(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)piperidine (1354826-65-5) → (2S,3S,4R,5R,6R)-2-allyl-6-azido-1-benzyl-3,4,5-tris(benzyloxy)azepane (1354826-75-7) + (2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine (1354826-74-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 4h;

DOI:10.1021/ol203385w

Reference yield: 32.0%

(3R,4R,5R,6S,7S) 7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-ol (1354826-63-3) → (2S,3S,4R,5R,6R)-2-allyl-6-azido-1-benzyl-3,4,5-tris(benzyloxy)azepane (1354826-75-7) + (2S,3S,4R,5R,6S)-2-allyl-6-(azidomethyl)-1-benzyl-3,4,5-tris(benzyloxy)piperidine (1354826-74-6)

Guidance literature:

With diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20 ℃; for 3h;

DOI:10.1021/ol203385w

upstream raw materials:

(3R,4R,5R,6S,7S) 7-allyl-4,5,6-tris(benzyloxy)azepan-3-ol

(3R,4R,5R,6S,7S) 7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-ol

(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)piperidine

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester