(E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate

Base Information

• Chemical Name: (E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate
• CAS No.: 71841-10-6
• Molecular Formula: C₂₉H₃₈O₄S
• Molecular Weight: 482.684
• Mol file: 71841-10-6.mol

Synonyms:(E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate

Chemical Property of (E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate

There total 7 articles about (E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate 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:

benzyloxyacetoaldehyde (60656-87-3) + (E)-methyl 6,10-dimethyl-2-(phenylthio)-5,9-undecadienoate (71841-09-3) → (E)-(2RS,1'SR)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate (71841-11-7) + (E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate (71841-10-6)

Guidance literature:

With zinc(II) chloride; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 1) -78 deg C, THF, 2) 0 deg C, 10 min;

DOI:10.1021/jo01306a002

Reference yield:

homogeraniol p-toluenesulfonate ester (71841-08-2) → (E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate (71841-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / dimethylsulfoxide / Ambient temperature

2: LDA, ZnCl₂ / tetrahydrofuran / 0.17 h / 0 °C

With zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/ja00388a038

Reference yield:

methyl 1-(phenylthio)acetate lithium enolate (115391-97-4) → (E)-(2RS,1'RS)-methyl 6,10-dimethyl-2-<2'-(benzyloxy)-1'-hydroxyethyl>-2-(phenylthio)-5,9-undecadienoate (71841-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / dimethylsulfoxide / Ambient temperature

2: LDA, ZnCl₂ / tetrahydrofuran / 0.17 h / 0 °C

With zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/ja00388a038

upstream raw materials:

benzyloxyacetoaldehyde

(E)-methyl 6,10-dimethyl-2-(phenylthio)-5,9-undecadienoate

methyl (phenylsulfanyl)acetate

homogeraniol p-toluenesulfonate ester

Downstream raw materials:

(2(1')E,5E)-methyl 2-(2'-benzyloxyethylidene)-6,10-dimethyl-5,9-undecadienoate