(3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol

Base Information

Chemical Name:(3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol
CAS No.:115483-02-8
Molecular Formula:C₂₅H₄₂O₂Si₂
Molecular Weight:430.778
Hs Code.:

Synonyms:(3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol

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Chemical Property of (3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol

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Technology Process of (3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol

There total 9 articles about (3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol 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%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 115483-01-7
(3R,4S)-1-O-benzyl-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol

: 115483-02-8
(3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 30 ℃; for 40h;

Reference yield:

: 106757-57-7
(R,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)prop-2-en-1-ol

: 115483-02-8
(3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1: 17.0 g / propionic acid / 1 h / 150 - 160 °C

2: 99 percent / 1.2M diisobutylaluminium hydride in toluene / toluene / 0.17 h / -15 °C

3: 1.) NaH / 1.) DMF, 30 deg C, 2 h; 2.) DMF, 3 h

4: 90 percent / p-toluenesulfonic acid / methanol / 12 h / 22 °C

5: 91 percent / pyridine / diethyl ether / 40 h / 22 °C

6: 91 percent / NaOMe / CH₂Cl₂ / 0.25 h / 0 °C

7: 1.) 1.6M C₄H₉Li/hexane / 1.) THF, -78 deg C; 2.) THF, reflux, 40 h

8: 90 percent / imidazole / dimethylformamide / 40 h / 30 °C

With pyridine; 1H-imidazole; hexane; sodium methylate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; propionic acid; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 100-44-7
benzyl chloride

: 115483-02-8
(3R,4S)-1-O-benzyl-4-O-(tert-butyldimethylsilyl)-7-trimethylsilyl-3-vinyl-6-heptyn-1,4-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, 30 deg C, 2 h; 2.) DMF, 3 h

2: 90 percent / p-toluenesulfonic acid / methanol / 12 h / 22 °C

3: 91 percent / pyridine / diethyl ether / 40 h / 22 °C

4: 91 percent / NaOMe / CH₂Cl₂ / 0.25 h / 0 °C

5: 1.) 1.6M C₄H₉Li/hexane / 1.) THF, -78 deg C; 2.) THF, reflux, 40 h

6: 90 percent / imidazole / dimethylformamide / 40 h / 30 °C

With pyridine; 1H-imidazole; hexane; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;