(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate

Base Information

• Chemical Name: (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate
• CAS No.: 1177263-65-8
• Molecular Formula: C₂₅H₃₇Cl₃O₅
• Molecular Weight: 523.925
• Mol file: 1177263-65-8.mol

Synonyms:(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate

Chemical Property of (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate

There total 14 articles about (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate 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: 100.0%

2,2,2-Trichloroethyl chloroformate (17341-93-4) + (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-ol (676324-80-4) → (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate (1177263-65-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/asia.200800365

Reference yield:

C18H28O4 → (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate (1177263-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene / 6.25 h / -78 °C / Molecular sieve

1.2: 0.5 h / 0 °C

2.1: pyridine; dmap / dichloromethane / 1 h / 0 °C

With pyridine; dmap; In dichloromethane; toluene;

DOI:10.1021/ml200176m

Reference yield:

4-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-hexan-2-ol → (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate (1177263-65-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine; methanesulfonyl chloride / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

2.1: potassium tert-butylate / toluene / 1 h / Reflux; Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Molecular sieve

4.1: triethylamine / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

5.1: titanium(IV) isopropylate / dichloromethane / 1 h / Inert atmosphere; Reflux

5.2: 4 h / Inert atmosphere; Reflux

6.1: copper(l) cyanide / diethyl ether / 2.33 h / -78 °C / Inert atmosphere

6.2: 2.33 h / -78 - -20 °C

7.1: trimethylaluminum / dichloromethane; Hexachlorobutadiene / -78 - 20 °C / Inert atmosphere

8.1: trifluorormethanesulfonic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 °C / Inert atmosphere

10.1: scandium tris(trifluoromethanesulfonate) / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

11.1: dmap / dichloromethane; pyridine / 1 h / 0 °C / Inert atmosphere

With titanium(IV) isopropylate; dmap; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; trimethylaluminum; copper(l) cyanide; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; Hexachlorobutadiene; toluene;

DOI:10.1021/jm4019965

upstream raw materials:

2,2,2-Trichloroethyl chloroformate

(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-ol

pivalaldehyde

(3S)-2,2-dimethyl-5-hexen-3-ol

Downstream raw materials:

apratoxin S₅

apratoxin S₄

apratoxin S₆