(3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol

Base Information

Chemical Name:(3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol
CAS No.:1197349-20-4
Molecular Formula:C₂₆H₃₈O₂Si
Molecular Weight:410.672
Hs Code.:

Synonyms:(3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol

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Chemical Property of (3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol

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Technology Process of (3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol

There total 6 articles about (3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol 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: 78.0%

: 945903-61-7
(3S,4S)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al

: 624-64-6
trans-2-Butene

: 1197349-20-4
(3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol

Guidance literature:: trans-2-Butene; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -78 - -45 ℃; Inert atmosphere;

With (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

(3S,4S)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al; optical yield given as %de; Further stages;
DOI:10.1039/c0cc00915f

Reference yield:

: 945903-61-7
(3S,4S)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al

: 99687-40-8,106357-20-4,106357-33-9,99745-86-5
(R,R)-[(E)-2-butenyl]diisopropyl tartrate boronate

: 1197349-20-4
(3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol

: (6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol

Guidance literature:: (3S,4S)-4-tert-butyldiphenylsilyloxy-3-methyl-pentan-1-al; (R,R)-[(E)-2-butenyl]diisopropyl tartrate boronate; In toluene; at -78 ℃; for 3h; Inert atmosphere; Molecular sieve;

With water; potassium carbonate; In toluene; at -78 - 20 ℃; for 2h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.06.025

Reference yield:

: 1197349-14-6
C₂₄H₃₂O₃Si

: 1197349-20-4
(3S,4R,6S,7S)-7-((tert-butyldiphenylsilyl)oxy)-3,6-dimethyloct-1-en-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 0.67 h / -78 - 20 °C / Inert atmosphere

3.1: (2R,5R)-(+)-2-tert-butyl-3-methyl-5-benzyl-4-imidazolidinone; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; trifluoroacetic acid / chloroform / 72 h / -30 °C / Inert atmosphere

4.1: toluene / 3 h / -78 °C / Inert atmosphere; Molecular sieve

4.2: 2 h / -78 - 20 °C / Inert atmosphere

With (2R,5R)-(+)-2-tert-butyl-3-methyl-5-benzyl-4-imidazolidinone; oxalyl dichloride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; diisobutylaluminium hydride; dimethyl sulfoxide; trifluoroacetic acid; In dichloromethane; chloroform; toluene; 2.1: Swern oxidation / 2.2: Swern oxidation / 4.1: Roush crotylation;
DOI:10.1016/j.tet.2011.06.025