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

Base Information

• Chemical Name: (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)piperidine
• CAS No.: 1354826-65-5
• Molecular Formula: C₃₇H₄₀ClNO₃
• Molecular Weight: 582.183
• Mol file: 1354826-65-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)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: 76.0%

(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-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)piperidine (1354826-65-5)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/acs.orglett.0c00503

Reference yield: 72.0%

(3R,4R,5R,6S,7S) 7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-ol (1354826-63-3) + methanesulfonyl chloride (124-63-0) → (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)piperidine (1354826-65-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol203385w

Reference yield:

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α,β-D-glucopyranose → (2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(chloromethyl)piperidine (1354826-65-5)

Guidance literature:

Multi-step reaction with 4 steps

1: solid supported triphenylphosphine / tetrahydrofuran / 40 °C

2: tetrahydrofuran / 1 h / 0 - 20 °C

3: potassium carbonate / N,N-dimethyl-formamide / 14 h / 20 °C

4: triethylamine / dichloromethane / 1 h / 0 °C

With potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Staudinger/aza-wittig alkylation;

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

methanesulfonyl chloride

β-D-glucose pentaacetate

Downstream raw materials:

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

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