(Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid

Base Information

• Chemical Name: (Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid
• CAS No.: 100333-60-6
• Molecular Formula: C₃₀H₄₂O₅Si
• Molecular Weight: 510.746
• Mol file: 100333-60-6.mol

Synonyms:(Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid

Chemical Property of (Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid

There total 2 articles about (Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid 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:

6-carboxy hexylidene triphenylphosphorane (53036-80-9) + 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3) → (Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid (100333-60-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 20 ℃; for 2.5h;

DOI:10.1021/jo00356a004

Reference yield:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal (93292-41-2) → (Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid (100333-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / AgNO₃, N-chlorosuccinimide (NCS) / acetonitrile; H₂O / 0.17 h / -20 °C

2: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 2.5 h / -78 - 20 °C

With N-chloro-succinimide; silver nitrate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetonitrile;

DOI:10.1021/jo00356a004

Reference yield:

(Z)-(S)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid (100333-60-6) → Benzoic acid (6Z,10E,12Z,15Z)-(S)-9-hydroxy-19-methoxycarbonyl-nonadeca-6,10,12,15-tetraenyl ester (100311-82-8)

Guidance literature:

Multi-step reaction with 9 steps

1: NaHCO₃ / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Ambient temperature

2: 68 percent / AlH₃*Et₂O / tetrahydrofuran / 0.5 h / 0 °C

3: 85 percent / Et₃N / CH₂Cl₂ / 0 °C

4: aq. TFA / tetrahydrofuran / Ambient temperature

5: Na₂CO₃, Pb(OAc)4 / CH₂Cl₂ / 0.25 h / -78 °C

6: toluene / 3 h / 80 °C

7: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C

8: NaHCO₃ / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature

9: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature

With lead(IV) acetate; aluminium hydride * diethyl ether; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; sodium carbonate; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene;

DOI:10.1021/jo00356a004

upstream raw materials:

6-carboxy hexylidene triphenylphosphorane

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal

Downstream raw materials:

methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate

Benzoic acid (6Z,10E,12Z,15Z)-(S)-9-hydroxy-19-methoxycarbonyl-nonadeca-6,10,12,15-tetraenyl ester

3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5(Z)-undecene-1,2(R),3(S),11-tetrol

Benzoic acid (Z)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-10-oxo-dec-6-enyl ester

Refernces