(4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol

Base Information

• Chemical Name: (4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol
• CAS No.: 326494-55-7
• Molecular Formula: C₂₂H₂₈O₃
• Molecular Weight: 340.463
• Mol file: 326494-55-7.mol

Synonyms:(4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol

Chemical Property of (4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol

There total 13 articles about (4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol 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:

tert-butyl-{3-[1-(4-methoxy-benzyloxy)-2-methyl-3-phenyl-propyl]-but-3-enyloxy}-dimethyl-silane (1026320-43-3) → (4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol (326494-55-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol (326494-55-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 90 percent / CF₃SO₃H / cyclohexane / 0 - 20 °C

2.1: 60 percent / iPrMgBr / tetrahydrofuran / -10 °C

3.1: 92 percent / tBuLi / diethyl ether; hexane / -78 °C

4.1: 93 percent / Zn(BH₄)2 / diethyl ether / -78 - -30 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

6.1: BuLi / tetrahydrofuran / -78 - -30 °C

7.1: TBAF / tetrahydrofuran / 20 °C

8.1: p-TsOH / benzene / 20 °C

8.2: aq. HCl / tetrahydrofuran / 0 °C

9.1: imidazole / CH₂Cl₂ / 20 °C

10.1: 85 percent / Li; NH₃ / -78 - -30 °C

11.1: CF₃SO₃H / CH₂Cl₂; cyclohexane / 0 °C

12.1: TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; zinc(II) tetrahydroborate; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; ammonia; tert.-butyl lithium; isopropylmagnesium bromide; lithium; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; benzene; 6.1: ether <1,2> Wittig rearrangement;

DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (4S,5R)-4-(4-Methoxy-benzyloxy)-5-methyl-3-methylene-6-phenyl-hexan-1-ol (326494-55-7)

Guidance literature:

Multi-step reaction with 2 steps

1: CF₃SO₃H / CH₂Cl₂; cyclohexane / 0 °C

2: TBAF / tetrahydrofuran / 20 °C

With trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO;2-K

upstream raw materials:

tert-butyl-{3-[1-(4-methoxy-benzyloxy)-2-methyl-3-phenyl-propyl]-but-3-enyloxy}-dimethyl-silane

O-benzyl 2,2,2-trichloroacetimidate

O-(4-methoxybenzyl)-trichloroacetimidate

methyl (S)-2-(benzyloxy)propanoate

Downstream raw materials:

1-[(S)-4-Iodo-2-methylene-1-((R)-1-methyl-2-phenyl-ethyl)-butoxymethyl]-4-methoxy-benzene