(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

Base Information

Chemical Name:(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
CAS No.:860295-53-0
Molecular Formula:C₂₆H₄₂O₃Si
Molecular Weight:430.703
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 90.0%

: 860295-67-6
(4S,5S,6S)-4-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-6-((S)-3,3-dibromo-1-methyl-allyl)-5-methyl-[1,3,2]dioxasilinane

: 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:: With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; for 0.5h;
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

Reference yield:

: 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

: 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 4 steps

1: 92 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

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

3: 1.15 g / Ph₃P; pyridine / CH₂Cl₂ / 0.5 h / 0 °C

4: 90 percent / nBuLi / tetrahydrofuran; hexane / 0.5 h / -30 °C

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