(5Z,9E,11E,13Z)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester

Base Information

• Chemical Name: (5Z,9E,11E,13Z)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester
• CAS No.: 93292-67-2
• Molecular Formula: C₅₃H₇₀O₄Si₂
• Molecular Weight: 827.307
• Mol file: 93292-67-2.mol

Synonyms:

Chemical Property of (5Z,9E,11E,13Z)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,9E,11E,13Z)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester

There total 14 articles about (5Z,9E,11E,13Z)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl 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:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3) → (5Z,9E,11E,13Z)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester (93292-67-2)

Guidance literature:

Multi-step reaction with 5 steps

2: H₂

3: aq. acid

4: lead tetraacetate

With lead(IV) acetate; hydrogen;

DOI:10.1016/0040-4039(84)80003-9

Reference yield:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal (93292-41-2) → (5Z,9E,11E,13Z)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester (93292-67-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / N-chlorosuccinimide, silver (I) nitrate

3: H₂

4: aq. acid

5: lead tetraacetate

With lead(IV) acetate; N-chloro-succinimide; hydrogen; silver nitrate;

DOI:10.1016/0040-4039(84)80003-9

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (5Z,9E,11E,13Z)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester (93292-67-2)

Guidance literature:

Multi-step reaction with 10 steps

1: lithium hexamethyldisilazide (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide

4: 77 percent / aq. acid

5: 95 percent / lead tetraacetate / CH₂Cl₂ / -78 °C

6: 81 percent

7: 2.) sodium borohydride/ceric chloride / 2.) isopropanol

8: 1.) DIPHOS, carbon tetrabromide / 2.) triphenylphosphine

9: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide

With lead(IV) acetate; sodium tetrahydroborate; ceric chloride; carbon tetrabromide; temephos; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1016/0040-4039(84)80003-9

upstream raw materials:

tert-Butyl-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hexyloxy]-diphenyl-silane

(4-carboxybutyl)triphenylphosphonium bromide

(2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-octane-1,2-diol

(4-carboxybutylene)triphenylphosphorane