(3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-4-ol

Base Information

Chemical Name:(3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-4-ol
CAS No.:362675-43-2
Molecular Formula:C₁₉H₂₆O₄
Molecular Weight:318.413
Hs Code.:

Synonyms:(3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-4-ol

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Chemical Property of (3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-4-ol

Chemical Property:

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Technology Process of (3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-4-ol

There total 11 articles about (3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-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:

: 2,2-Dimethyl-propionic acid (4S,5S)-5-benzyloxy-4-(tert-butyl-diphenyl-silanyloxy)-hept-6-ynyl ester

: 362675-43-2
(3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-4-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1021/jo0104532

Reference yield:

: 362675-40-9
(2S,3S)-(-)-2-benzyloxy-3,4-epoxy-1-(tert-butyldimethyldimethylsiloxy)butane

: 362675-43-2
(3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran / 0.08 h / -78 °C

2.1: imidazole / dimethylformamide / 4.5 h / 20 °C

2.2: K₂CO₃ / methanol / 1 h

3.1: 2.44 g / H₂; pyridine / Pd/Ba₂CO₃ / ethyl acetate / 4.5 h / 20 °C

4.1: BH₃*THF / tetrahydrofuran / 1 h / 20 °C

4.2: aq. NaOH; aq. H₂O₂ / tetrahydrofuran; H₂O / 1 h / 20 °C

5.1: Et₃N; dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

5.2: 426 mg / pyridinium p-toluenesulfonate / methanol / 24 h / 20 °C

6.1: DMSO; oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

6.2: triethylamine / CH₂Cl₂ / -78 - 20 °C

7.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

8.1: EtMgBr / tetrahydrofuran / 0.17 h / -20 °C

9.1: 224 mg / n-tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

With pyridine; 1H-imidazole; dmap; n-butyllithium; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 6.1: Swern oxidation;
DOI:10.1021/jo0104532

Reference yield:

: (2S,3S)-3-benzyloxy-4-[tert-butyl(dimethyl)silyloxy]butane-1,2-diol

: 362675-43-2
(3S,4S)-(+)-3-benzyloxy-7-(pivaloyloxy)-1-heptyn-4-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: pyridine / 8 h

1.2: 63 percent / K₂CO₃ / methanol / 1 h

2.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran / 0.08 h / -78 °C

3.1: imidazole / dimethylformamide / 4.5 h / 20 °C

3.2: K₂CO₃ / methanol / 1 h

4.1: 2.44 g / H₂; pyridine / Pd/Ba₂CO₃ / ethyl acetate / 4.5 h / 20 °C

5.1: BH₃*THF / tetrahydrofuran / 1 h / 20 °C

5.2: aq. NaOH; aq. H₂O₂ / tetrahydrofuran; H₂O / 1 h / 20 °C

6.1: Et₃N; dimethylaminopyridine / CH₂Cl₂ / 4 h / 20 °C

6.2: 426 mg / pyridinium p-toluenesulfonate / methanol / 24 h / 20 °C

7.1: DMSO; oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

7.2: triethylamine / CH₂Cl₂ / -78 - 20 °C

8.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

9.1: EtMgBr / tetrahydrofuran / 0.17 h / -20 °C

10.1: 224 mg / n-tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

With pyridine; 1H-imidazole; dmap; n-butyllithium; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium; In tetrahydrofuran; pyridine; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 7.1: Swern oxidation;
DOI:10.1021/jo0104532