(5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol

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Chemical Name:(5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol
CAS No.:157240-49-8
Molecular Formula:C₃₆H₅₀O₆Si
Molecular Weight:606.875
Hs Code.:
Mol file:157240-49-8.mol

Synonyms:(5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol

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Chemical Property of (5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol Edit

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Technology Process of (5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol

There total 16 articles about (5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol 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: 96.0%

: 214533-11-6
(5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-1,2-isopropylidenedioxy-8-(4-methoxybenzyloxy)-10-methyl-5-undecen-4-ol

: 157240-49-8
(5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol

Guidance literature:: With methanol; acetic acid; for 24h; Ambient temperature;
DOI:10.1248/cpb.46.1199

Reference yield:

: 95514-04-8
(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

: 157240-49-8
(5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol

Guidance literature:: Multi-step reaction with 13 steps

1: 100 percent / p-dimethylaminopyridine / CH₂Cl₂ / 5 h / Ambient temperature

2: 92 percent / dimethylsulfoxide / 2 h / 50 °C

3: 1.) DIBAH, 2.) aq. HCl, Rochelle salt / 1.) CH₂Cl₂, THF, -78 deg C, 40 min, 2.) CH₂Cl₂, THF, Et₂O, RT, 12 h

4: CH₂Cl₂ / 10 h / Ambient temperature

5: 100 percent / DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

6: 90 percent / (iso-PrO)4Ti, L-(+)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

7: 98 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

8: p-TsOH*H₂O / benzene / 3 h / Ambient temperature

9: DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

10: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -30 deg C, 1 h

11: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, RT, 1 h

12: 97 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

13: 96 percent / AcOH, MeOH / 24 h / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; rochelle salt; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1248/cpb.46.1199

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 157240-49-8
(5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-8-(4-methoxybenzyloxy)-10-methyl-5-undecene-1,2,4-triol

Guidance literature:: Multi-step reaction with 14 steps

1: Ca(BH₄)2 / ethanol / 15 h / Ambient temperature

2: 100 percent / p-dimethylaminopyridine / CH₂Cl₂ / 5 h / Ambient temperature

3: 92 percent / dimethylsulfoxide / 2 h / 50 °C

4: 1.) DIBAH, 2.) aq. HCl, Rochelle salt / 1.) CH₂Cl₂, THF, -78 deg C, 40 min, 2.) CH₂Cl₂, THF, Et₂O, RT, 12 h

5: CH₂Cl₂ / 10 h / Ambient temperature

6: 100 percent / DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

7: 90 percent / (iso-PrO)4Ti, L-(+)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

8: 98 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

9: p-TsOH*H₂O / benzene / 3 h / Ambient temperature

10: DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

11: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -30 deg C, 1 h

12: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, RT, 1 h

13: 97 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

14: 96 percent / AcOH, MeOH / 24 h / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; calcium borohydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; rochelle salt; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium iodide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1248/cpb.46.1199