Toluene-4-sulfonic acid (3S,4R)-4-(2-methoxy-ethoxymethoxy)-3,7-dimethyl-oct-6-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3S,4R)-4-(2-methoxy-ethoxymethoxy)-3,7-dimethyl-oct-6-enyl ester
• CAS No.: 84071-66-9
• Molecular Formula: C₂₁H₃₄O₆S
• Molecular Weight: 414.563
• Mol file: 84071-66-9.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (3S,4R)-4-(2-methoxy-ethoxymethoxy)-3,7-dimethyl-oct-6-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3S,4R)-4-(2-methoxy-ethoxymethoxy)-3,7-dimethyl-oct-6-enyl ester

There total 11 articles about Toluene-4-sulfonic acid (3S,4R)-4-(2-methoxy-ethoxymethoxy)-3,7-dimethyl-oct-6-enyl ester 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:

(4S,5S)-5-(iodomethyl)-4-methyldihydrofuran-2(3H)-one (74035-91-9) → Toluene-4-sulfonic acid (3S,4R)-4-(2-methoxy-ethoxymethoxy)-3,7-dimethyl-oct-6-enyl ester (84071-66-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / Na₂CO₃ / methanol

2: 10 molpercent CuBr / tetrahydrofuran / -20 °C

3: LAH

4: C₅H₅N

5: i-PrNEt

6: 80percent AcOH

7: C₅H₅N

With pyridine; lithium aluminium tetrahydride; i-PrNEt; sodium carbonate; acetic acid; copper(I) bromide; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)87623-6

Reference yield:

(4R)-5-methoxycarbonyl-4-methylvaleric acid (71685-51-3) → Toluene-4-sulfonic acid (3S,4R)-4-(2-methoxy-ethoxymethoxy)-3,7-dimethyl-oct-6-enyl ester (84071-66-9)

Guidance literature:

Multi-step reaction with 10 steps

1: Pb(OAc)4, Cu(OAc)2 / benzene / Heating

2: 10percent KOH

3: 75 percent / I₂ / acetonitrile / 72 h / -20 °C

4: 80 percent / Na₂CO₃ / methanol

5: 10 molpercent CuBr / tetrahydrofuran / -20 °C

6: LAH

7: C₅H₅N

8: i-PrNEt

9: 80percent AcOH

10: C₅H₅N

With pyridine; lead(IV) acetate; potassium hydroxide; lithium aluminium tetrahydride; copper diacetate; i-PrNEt; iodine; sodium carbonate; acetic acid; copper(I) bromide; In tetrahydrofuran; methanol; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)87623-6

Reference yield:

methyl (R)-(+)-citronellate (20425-48-3) → Toluene-4-sulfonic acid (3S,4R)-4-(2-methoxy-ethoxymethoxy)-3,7-dimethyl-oct-6-enyl ester (84071-66-9)

Guidance literature:

Multi-step reaction with 12 steps

1: O₃

2: Jones oxidation

3: Pb(OAc)4, Cu(OAc)2 / benzene / Heating

4: 10percent KOH

5: 75 percent / I₂ / acetonitrile / 72 h / -20 °C

6: 80 percent / Na₂CO₃ / methanol

7: 10 molpercent CuBr / tetrahydrofuran / -20 °C

8: LAH

9: C₅H₅N

10: i-PrNEt

11: 80percent AcOH

12: C₅H₅N

With pyridine; lead(IV) acetate; potassium hydroxide; lithium aluminium tetrahydride; copper diacetate; i-PrNEt; iodine; sodium carbonate; ozone; acetic acid; copper(I) bromide; In tetrahydrofuran; methanol; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)87623-6

upstream raw materials:

(4S,5S)-5-(iodomethyl)-4-methyldihydrofuran-2(3H)-one

(4R)-5-methoxycarbonyl-4-methylvaleric acid

methyl (R)-(+)-citronellate

methyl 3(R),7-dimethyl-6,7-epoxyoctanoate

Downstream raw materials:

1-[(E)-(5R,6S,14R)-16-Benzyloxy-5-(2-methoxy-ethoxymethoxy)-2,6,10,14-tetramethyl-hexadeca-2,10-diene-8-sulfonyl]-4-methyl-benzene

(3S,4R)-4-(2-methoxyethoxy)methoxy-3,7-dimethyl-1-(4-methylphenyl)sulfonyl-6-octene