tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate

Base Information

• Chemical Name: tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate
• CAS No.: 157394-53-1
• Molecular Formula: C₁₈H₂₉NO₃
• Molecular Weight: 307.433
• Mol file: 157394-53-1.mol

Synonyms:tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate

Chemical Property of tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate

There total 3 articles about tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate 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: 80.0%

n-butyllithium (109-72-8,29786-93-4) + Boc-L-phenylalaninal (72155-45-4) → tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate (157394-53-1) + tert-butyl (2S,3S)-3-hydroxy-1-phenylheptan-2-ylcarbamate (157394-65-5)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In diethyl ether; hexane; at -78 ℃; for 4h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)73024-3

Reference yield:

tert-butyl (S)-3-oxo-1-phenylheptan-2-ylcarbamate (1277097-52-5) → tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate (157394-53-1) + tert-butyl (2S,3S)-3-hydroxy-1-phenylheptan-2-ylcarbamate (157394-65-5)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -78 ℃; for 24h;

Reference yield:

Boc-Phe-OH N,O-dimethyl hydroxamate (87694-53-9) → tert-butyl (1S,2R)-1-benzyl-2-hydroxyhexylcarbamate (157394-53-1) + tert-butyl (2S,3S)-3-hydroxy-1-phenylheptan-2-ylcarbamate (157394-65-5)

Guidance literature:

Boc-Phe-OH N,O-dimethyl hydroxamate; (n-Bu)3M;

With sodium tetrahydroborate; In methanol; Further stages.;

DOI:10.1016/j.bmcl.2006.12.051

upstream raw materials:

n-butyllithium

Boc-L-phenylalaninal

Boc-Phe-OH N,O-dimethyl hydroxamate

tert-butyl (S)-3-oxo-1-phenylheptan-2-ylcarbamate

Downstream raw materials:

tert-butyl (1S,2S)-2-azido-1-benzylhexylcarbamate

Refernces

• 1、 -. "Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of alzheimer's disease". Page/Page column 17. . Retrieved 2008/06/13.