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

Base Information

• Chemical Name: methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate
• CAS No.: 100333-61-7
• Molecular Formula: C₃₁H₄₄O₅Si
• Molecular Weight: 524.773
• Mol file: 100333-61-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate 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) → methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate (100333-61-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hydrogencarbonate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00356a004

Reference yield:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3) → methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate (100333-61-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hydrogencarbonate; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00356a004

Reference yield:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal (93292-41-2) → methyl 9-O-(tert-butyldiphenylsilyl)-10,11-bis-O-(1-methylethylidene)-9(S),10(R),11-trihydroxy-6(Z)-undecenoate (100333-61-7)

Guidance literature:

Multi-step reaction with 3 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

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

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

DOI:10.1021/jo00356a004

upstream raw materials:

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

dimethyl sulfate

6-carboxy hexylidene triphenylphosphorane

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

Downstream raw materials:

Benzoic acid (6Z,10E,12Z,15Z)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-19-carboxy-nonadeca-6,10,12,15-tetraenyl ester

Benzoic acid (6Z,10E,12Z,15Z)-(S)-9-(tert-butyl-diphenyl-silanyloxy)-19-methoxycarbonyl-nonadeca-6,10,12,15-tetraenyl ester

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

Benzoic acid (Z)-(9S,10R)-9-(tert-butyl-diphenyl-silanyloxy)-10,11-dihydroxy-undec-6-enyl ester

Refernces