tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate

Base Information

• Chemical Name: tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate
• CAS No.: 156624-89-4
• Molecular Formula: C₁₉H₂₈O₄
• Molecular Weight: 320.429
• Mol file: 156624-89-4.mol

Synonyms:tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate

Chemical Property of tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate

There total 6 articles about tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate 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: 90.0%

tert-butyl (4S,5S,E)-5-hydroxy-4,6-dimethyl-3-oxo-7-phenylhept-6-enoate (156624-88-3) → tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate (156624-89-4)

Guidance literature:

tert-butyl (4S,5S,E)-5-hydroxy-4,6-dimethyl-3-oxo-7-phenylhept-6-enoate; With diethyl methoxy borane; In tetrahydrofuran; methanol; at -78 ℃; for 1h; Inert atmosphere;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -78 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c7gc03534a

Reference yield:

(E)-(2S,3S)-3-Hydroxy-2,4-dimethyl-5-phenyl-pent-4-enethioic acid S-phenyl ester (156624-87-2) → tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate (156624-89-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) TEA, N,N-dimethylaminopyridine / 1.) tetrahydrofuran, 90 min, 2.) tetrahydrofuran, -40 deg C, 30 min

2: 1M hydrochloric acid / acetone / 0.5 h / Ambient temperature

With hydrogenchloride; dmap; TEA; In acetone;

DOI:10.1016/S0040-4020(01)80796-1

Reference yield:

(E)-(4S,5S)-4,6-Dimethyl-3-oxo-7-phenyl-5-trimethylsilanyloxy-hept-6-enoic acid tert-butyl ester → tert-butyl (3S,4R,5S,E)-3,5-dihydroxy-4,6-dimethyl-7-phenylhept-6-enoate (156624-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1M hydrochloric acid / acetone / 0.5 h / Ambient temperature

With hydrogenchloride; In acetone;

DOI:10.1016/S0040-4020(01)80796-1

upstream raw materials:

tert-butyl (4S,5S,E)-5-hydroxy-4,6-dimethyl-3-oxo-7-phenylhept-6-enoate

(E)-(2S,3S)-3-Hydroxy-2,4-dimethyl-5-phenyl-pent-4-enethioic acid S-phenyl ester

α-methyl-trans-cinnamaldehyde

methyl (2S,3S,E)-3-hydroxy-2,4-dimethyl-5-phenylpent-4-enoate

Downstream raw materials:

(4S,5R,6S)-4-hydroxy-5-methyl-6-((E)-1-phenylprop-1-en-2-yl)tetrahydro-2H-pyran-2-one

(4S,5S,6S)-5-Methyl-6-((E)-1-methyl-2-phenyl-vinyl)-4-triisopropylsilanyloxy-tetrahydro-pyran-2-one