(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol

Base Information

Chemical Name:(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol
CAS No.:171524-13-3
Molecular Formula:C₃₃H₅₆O₆Si
Molecular Weight:576.89
Hs Code.:

(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<<dimethyl(2-methyl-2-propyl)silyl>oxy>-13-tetradecene-3,5,9,11-tetrol

Synonyms:(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol

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Chemical Property of (3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol

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Technology Process of (3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol

There total 26 articles about (3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol 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: 80.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 171524-12-2
(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-13-tetradecene-3,5,8,9,11-pentol

: 171524-13-3
(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.0333333h;
DOI:10.1021/jo00129a019

Reference yield:

: 171523-93-6
(2S,4R)-2-(N-Benzylamino)-4-<oxy>-6-hepten-1-ol

: 171524-13-3
(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol

Guidance literature:: Multi-step reaction with 15 steps

1: 100 percent / benzene; H₂O / 0.5 h / Heating

2: 95 percent / i-Bu₂AlH / toluene; hexane / 0.08 h / -60 °C

3: n-t-Bu₄NCl, 50percent aq. NaOH / CHCl₃ / 0.75 h / Ambient temperature

5: 5percent HCl / methanol / 0.08 h / Ambient temperature

6: 0.33 h / Ambient temperature

7: 4-methylmorpholine-N-oxide, OsO₄ / H₂O; 2-methyl-propan-2-ol / 12 h / Ambient temperature

8: aq. Na₂SO₃ / 0.75 h / Ambient temperature

9: 97 percent / n-Bu₃P / 1,2-dimethoxy-ethane / 24 h / Heating

10: 99 percent / magnesium monoperoxyphthalate / aq. ethanol / 0 °C

11: 66 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C to -60 deg C, 1 h, 2.) -78 deg C, 30 min

12: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

13: 89 percent / n-Bu₃SnH, AIBN / toluene / 0.17 h / Heating

14: 100 percent / LiHB(s-Bu)3 / tetrahydrofuran / -110 - 0 °C

15: 80 percent / 2,6-lutidine / CH₂Cl₂ / 0.03 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tributylphosphine; tetrabutyl-ammonium chloride; tri-n-butyl-tin hydride; L-Selectride; diisobutylaluminium hydride; Dess-Martin periodane; magnesium monoperoxyphthalate hexahydrate; 4-methylmorpholine N-oxide; sodium sulfite; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; chloroform; water; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/jo00129a019

Reference yield:

: 130459-42-6
(2S,4R)-2-(N-Benzyl-N-methylamino)-4-<oxy>-6-hepten-1-ol

: 171524-13-3
(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-tetradecene-3,5,9,11-tetrol

Guidance literature:: Multi-step reaction with 13 steps

1: n-t-Bu₄NCl, 50percent aq. NaOH / CHCl₃ / 0.75 h / Ambient temperature

3: 5percent HCl / methanol / 0.08 h / Ambient temperature

4: 0.33 h / Ambient temperature

5: 4-methylmorpholine-N-oxide, OsO₄ / H₂O; 2-methyl-propan-2-ol / 12 h / Ambient temperature

6: aq. Na₂SO₃ / 0.75 h / Ambient temperature

7: 97 percent / n-Bu₃P / 1,2-dimethoxy-ethane / 24 h / Heating

8: 99 percent / magnesium monoperoxyphthalate / aq. ethanol / 0 °C

9: 66 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C to -60 deg C, 1 h, 2.) -78 deg C, 30 min

10: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

11: 89 percent / n-Bu₃SnH, AIBN / toluene / 0.17 h / Heating

12: 100 percent / LiHB(s-Bu)3 / tetrahydrofuran / -110 - 0 °C

13: 80 percent / 2,6-lutidine / CH₂Cl₂ / 0.03 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tributylphosphine; tetrabutyl-ammonium chloride; tri-n-butyl-tin hydride; L-Selectride; Dess-Martin periodane; magnesium monoperoxyphthalate hexahydrate; 4-methylmorpholine N-oxide; sodium sulfite; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; chloroform; water; toluene; tert-butyl alcohol;
DOI:10.1021/jo00129a019