Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester
• CAS No.: 137132-01-5
• Molecular Formula: C₅₁H₇₆O₁₀SSi
• Molecular Weight: 909.31
• Mol file: 137132-01-5.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester

There total 25 articles about Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl 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:

benzyl bromide (100-39-0) → Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester (137132-01-5)

Guidance literature:

Multi-step reaction with 15 steps

2: AcOH / tetrahydrofuran; H₂O / 50 °C

3: imidazole / dimethylformamide

4: 90 percent / t-BuOOH / (+)-DIPT, Ti(i-PrO)4 / CH₂Cl₂ / -20 °C

5: NaH / tetrahydrofuran / 0 °C

6: n-Bu₄NF / tetrahydrofuran

7: Dess-Martin periodinane reagent

8: tetrahydrofuran

9: H₂ / Pd/C / ethyl acetate

10: 1.) NaOH / 2.) CSA / 1.) EtOH, reflux; 2.) CH₂Cl₂

11: boron trifluoride etherate / 0 °C

12: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

13: 93 percent / LiAlH₄ / tetrahydrofuran / -20 °C

14: Et₃N / DMAP / CH₂Cl₂

15: 2,6-lutidine / CH₂Cl₂

With 1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; palladium on activated charcoal; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)70631-9

Reference yield:

3-(p-methoxybenzyloxy)propanal (128461-65-4) → Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester (137132-01-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) (c-C₅H₉)2OTf, i-Pr₂NEt / 2.) CH₂Cl₂, -78 deg C

2: 92 percent / DDQ / CH₂Cl₂

3: 1.) LiOH, H₂O₂; 2.) LiAlH₄ / 1.) THF, H₂O; 2.) THF, 0 deg C

4: (ClCO)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 °C

5: tetrahydrofuran

7: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

8: 93 percent / LiAlH₄ / tetrahydrofuran / -20 °C

9: Et₃N / DMAP / CH₂Cl₂

10: 2,6-lutidine / CH₂Cl₂

With lithium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; (c-C₅H₉)2OTf; dihydrogen peroxide; sodium hexamethyldisilazane; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,6-dimethylpyridine; dmap; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)70631-9

Reference yield:

Propionic acid (R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-allyl ester → Toluene-4-sulfonic acid (E)-(2S,6R)-2-[(2S,3S,4S,6R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethoxy-6-methyl-heptyl]-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester (137132-01-5)

Guidance literature:

Multi-step reaction with 15 steps

2: AcOH / tetrahydrofuran; H₂O / 50 °C

3: imidazole / dimethylformamide

4: 90 percent / t-BuOOH / (+)-DIPT, Ti(i-PrO)4 / CH₂Cl₂ / -20 °C

5: NaH / tetrahydrofuran / 0 °C

6: n-Bu₄NF / tetrahydrofuran

7: Dess-Martin periodinane reagent

8: tetrahydrofuran

9: H₂ / Pd/C / ethyl acetate

10: 1.) NaOH / 2.) CSA / 1.) EtOH, reflux; 2.) CH₂Cl₂

11: boron trifluoride etherate / 0 °C

12: 80 percent / sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

13: 93 percent / LiAlH₄ / tetrahydrofuran / -20 °C

14: Et₃N / DMAP / CH₂Cl₂

15: 2,6-lutidine / CH₂Cl₂

With 1H-imidazole; tert.-butylhydroperoxide; sodium hydroxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; palladium on activated charcoal; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)70631-9

upstream raw materials:

t-butyldimethylsiyl triflate

Toluene-4-sulfonic acid (E)-(2S,6R)-2-((2S,3S,4S,6R)-7-benzyloxy-3-hydroxy-2,4-dimethoxy-6-methyl-heptyl)-6-[(2R,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4-methyl-nona-4,8-dienyl ester

benzyl bromide

3-(p-methoxybenzyloxy)propanal

Downstream raw materials:

{(E)-(1R,2S,4S,8R)-1-((1S,3R)-4-Benzyloxy-1-methoxy-3-methyl-butyl)-2-methoxy-8-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-4,6-dimethyl-undeca-6,10-dienyloxy}-tert-butyl-dimethyl-silane