(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

Base Information

Chemical Name:(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene
CAS No.:794516-11-3
Molecular Formula:C₂₂H₃₄O₅Si
Molecular Weight:406.594
Hs Code.:

Synonyms:(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

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Chemical Property of (3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

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Technology Process of (3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

There total 7 articles about (3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene 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:

: Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

: 794516-11-3
(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 1h;
DOI:10.1021/jo0491051

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 794516-11-3
(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 2.1 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 91 percent / BaCO₃; NBS / CCl₄ / Heating

3: 86 percent / Zn; NaBH₃CN / propan-1-ol; H₂O / 95 °C

4: pyridine / 20 °C

5: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C

With pyridine; dmap; N-Bromosuccinimide; sodium cyanoborohydride; triethylamine; barium carbonate; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; propan-1-ol; tetrachloromethane; dichloromethane; water;
DOI:10.1021/jo0491051

Reference yield:

: 299410-93-8
methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

: 794516-11-3
(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 2.1 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

2: 91 percent / BaCO₃; NBS / CCl₄ / Heating

3: 86 percent / Zn; NaBH₃CN / propan-1-ol; H₂O / 95 °C

4: pyridine / 20 °C

5: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C

With pyridine; dmap; N-Bromosuccinimide; sodium cyanoborohydride; triethylamine; barium carbonate; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; propan-1-ol; tetrachloromethane; dichloromethane; water;
DOI:10.1021/jo0491051