2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester
CAS No.:860478-32-6
Molecular Formula:C₂₂H₃₆O₅
Molecular Weight:380.525
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester

There total 1 articles about 2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl 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: 94.0%

: 618096-11-0
2,2-Dimethyl-propionic acid (2S,3S,4S,5S,6S)-7-benzyloxy-3-hydroxy-2,4,6-trimethyl-5-triethylsilanyloxy-heptyl ester

: 860478-32-6
2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol050864v

Reference yield: 74.0%

: 860478-32-6
2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester

: 85272-31-7
di-tert-butylsilyl bis(trifluoromethanesulfonate)

: 860295-66-5
2,2-Dimethyl-propionic acid (S)-2-[(4S,5R,6S)-6-((S)-2-benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-propyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 30 ℃; for 66h;
DOI:10.1021/ol050864v

Reference yield:

: 860478-32-6
2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-7-benzyloxy-3,5-dihydroxy-2,4,6-trimethyl-heptyl ester

: 860295-53-0
(4S,5S,6S)-4-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-6-((S)-1-methyl-prop-2-ynyl)-[1,3,2]dioxasilinane

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / 2,6-lutidine / CH₂Cl₂ / 66 h / 30 °C

2: 92 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 1.15 g / Ph₃P; pyridine / CH₂Cl₂ / 0.5 h / 0 °C

5: 90 percent / nBuLi / tetrahydrofuran; hexane / 0.5 h / -30 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 3: Swern oxidation / 4: Wittig reaction;
DOI:10.1021/ol050864v