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

Base Information Edit

Chemical Name:(5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-1,2-isopropylidenedioxy-8-(4-methoxybenzyloxy)-10-methyl-5-undecen-4-ol
CAS No.:214533-11-6
Molecular Formula:C₃₉H₅₄O₆Si
Molecular Weight:646.94
Hs Code.:
Mol file:214533-11-6.mol

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

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

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

There total 16 articles about (5E,2R,4S,8R,10R)-11-(tert-butyldiphenylsilyloxy)-1,2-isopropylidenedioxy-8-(4-methoxybenzyloxy)-10-methyl-5-undecen-4-ol 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: 97.0%

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

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

Guidance literature:: With lithium aluminium tetrahydride; lithium iodide; In diethyl ether; at -100 ℃; for 1h;
DOI:10.1248/cpb.46.1199

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 12 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

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diisobutylaluminium hydride; toluene-4-sulfonic 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:

: 112031-10-4
methyl (R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate

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

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, 30 min

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

3: 97 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

With lithium aluminium tetrahydride; n-butyllithium; lithium iodide; In diethyl ether;
DOI:10.1248/cpb.46.1199