(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-oxotridecane-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-oxotridecane-3,5,9,11-tetrol
CAS No.:171524-14-4
Molecular Formula:C₃₂H₅₄O₇Si
Molecular Weight:578.862
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-oxotridecane-3,5,9,11-tetrol

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

There total 30 articles about (3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-oxotridecane-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:

: 2-((4R,6R)-6-((R)-3-((4R,6S)-6-(2-(benzyloxy)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)-1-(tertbutyldimethylsilyloxy)propyl)-2,2-dimethyl-1,3-dioxan-4-yl)ethanol

: 171524-14-4
(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-oxotridecane-3,5,9,11-tetrol

Guidance literature:: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; In dichloromethane; at 0 ℃; for 0.5h; pH=8.6; aq. buffer; Large scale reaction;
DOI:10.1002/anie.200800589

Reference yield:

: [(R)-3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((4R,6R)-2,2-dimethyl-6-oxiranylmethyl-[1,3]dioxan-4-yl)-propoxy]-tert-butyl-dimethyl-silane

: 171524-14-4
(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-oxotridecane-3,5,9,11-tetrol

Guidance literature:: With sodium periodate; In ethanol; at 0 ℃; Yield given;
DOI:10.1021/jo00129a019

Reference yield:

: 130459-40-4
2-Phenyl-4(S)-(2(R)-hydroxypent-4-enyl)-2-oxazoline

: 171524-14-4
(3S,5S,8R,9R,11R)-1-(Benzyloxy)-3,5:9,11-di-O-isopropylidene-8-<oxy>-13-oxotridecane-3,5,9,11-tetrol

Guidance literature:: Multi-step reaction with 19 steps

1: 100 percent / NEt₃ / CH₂Cl₂ / 0.08 h / 0 °C

2: 92 percent / i-Bu₂AlH / toluene; hexane / 0.08 h / 0 °C

3: 100 percent / benzene; H₂O / 0.5 h / Heating

4: 95 percent / i-Bu₂AlH / toluene; hexane / 0.08 h / -60 °C

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

7: 5percent HCl / methanol / 0.08 h / Ambient temperature

8: 0.33 h / Ambient temperature

9: 4-methylmorpholine-N-oxide, OsO₄ / H₂O; 2-methyl-propan-2-ol / 12 h / Ambient temperature

10: aq. Na₂SO₃ / 0.75 h / Ambient temperature

11: 97 percent / n-Bu₃P / 1,2-dimethoxy-ethane / 24 h / Heating

12: 99 percent / magnesium monoperoxyphthalate / aq. ethanol / 0 °C

13: 66 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C to -60 deg C, 1 h, 2.) -78 deg C, 30 min

14: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

15: 89 percent / n-Bu₃SnH, AIBN / toluene / 0.17 h / Heating

16: 100 percent / LiHB(s-Bu)3 / tetrahydrofuran / -110 - 0 °C

17: 80 percent / 2,6-lutidine / CH₂Cl₂ / 0.03 h / 0 °C

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

19: sodium periodate / aq. ethanol / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; sodium periodate; 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; triethylamine; 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