tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

Base Information

• Chemical Name: tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate
• CAS No.: 1393792-97-6
• Molecular Formula: C₂₈H₃₉NO₄
• Molecular Weight: 453.622
• Mol file: 1393792-97-6.mol

Synonyms:tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

Chemical Property of tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

There total 9 articles about tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 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: 39.0%

tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate (1393792-88-5) + (S)-N-benzyl-1-phenylethylamine (17480-69-2) → tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate (1393792-97-6) + tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate (1393792-96-5)

Guidance literature:

(S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In diethyl ether; hexane; at -20 ℃; for 0.5h; Inert atmosphere;

tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate; In diethyl ether; hexane; at -20 ℃; for 5h; optical yield given as %de; Inert atmosphere;

DOI:10.1039/c2ob25099c

Reference yield:

tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate (1393792-88-5) + (S)-N-benzyl-1-phenylethylamine (17480-69-2) → tert-butyl (S,Z)-4,5-O-isopropylidene-4,5-dihydroxyhex-3-enoate (1393792-94-3) + tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate (1393792-97-6) + tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate (1393792-96-5)

Guidance literature:

(S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In diethyl ether; hexane; at -20 ℃; for 0.5h; Inert atmosphere;

tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate; In diethyl ether; hexane; at -20 ℃; for 5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1039/c2ob25099c

Reference yield:

(4R,5R)-4-(iodomethyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane (1393792-90-9) → tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate (1393792-97-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Reflux; Inert atmosphere

2.1: 2.27% Pd/C; hydrogen; triethylamine / methanol / 24 h / 20 °C / 760.05 Torr

3.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -20 °C / Inert atmosphere

3.2: 5 h / -20 °C / Inert atmosphere

With n-butyllithium; Hoveyda-Grubbs catalyst second generation; 2.27% Pd/C; hydrogen; triethylamine; In methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1039/c2ob25099c

upstream raw materials:

(4R,5R)-4-(iodomethyl)-2,2-dimethyl-5-vinyl-1,3-dioxolane

tert-butyl (R,R,E)-4,5-O-isopropylidene-4,5-dihydroxy-6-iodohex-2-enoate

tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate

(S)-N-benzyl-1-phenylethylamine

Refernces