<2S-(2R,3R,4R,5R,6S,8R,9R+,10S,11S,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)

Base Information

Chemical Name:<2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)
CAS No.:123992-27-8
Molecular Formula:C₆₃H₈₂O₆Si
Molecular Weight:963.426
Hs Code.:

<2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)

Synonyms:<2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)

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Chemical Property of <2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)

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Technology Process of <2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)

There total 24 articles about <2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36) 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: 58.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 123992-25-6
<2S-(2R*,3R*,4S*,5R*,6S*,8R*,9R*,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-5,9,11-tris(phenylmethoxy)-1,3-tridecanediol (Diol 34)

: 123992-27-8
<2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)

Guidance literature:: With pyridinium p-toluenesulfonate; Diisobutylaluminium hydride(1 M solution in tetrahydrofuran, 4.9 mL, 4.9 mmol); In dichloromethane; benzene; 1) reflux, 2h, 2) r.t. 1.5h;
DOI:10.1021/jo00292a045

Reference yield:

: 36019-62-2
2,3-Dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 4)

: 123992-27-8
<2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)

Guidance literature:: Multi-step reaction with 22 steps

1: 78 percent / 1) cerium trichloride heptahydrate, NaBH₄, 2) p-toluene sulfonic acid / ethanol / 1) -15 deg C, 2) r.t., 1h

2: 80 percent / borane-dimethyl sulfide complex, NaOH, 30percent H₂O₂ / tetrahydrofuran; dimethylsulfoxide / 4 h

3: 64 percent / TiCl₄ / CH₂Cl₂ / 1) 0 deg C, 2) r.t., 1.5h

4: 88 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

5: 100 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 8 h / Heating

6: NBS, NaHCO₃ / acetone; H₂O / -15 °C

7: 40 percent / 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 40 min, 2) reflux, 1h

8: 86 percent / cerium trichloride heptahydrate, NaBH₄ / ethanol / -15 °C

9: 91 percent / p-toluenesulfonic acid monohydrate / 2 h / Ambient temperature

10: 80 percent / H₂, 5percent Pd/Al / ethyl acetate / 36 h

11: 69 percent / TiCl₄ / CH₂Cl₂ / -78 °C

12: 94 percent / 95percent NaH, tetrabutylammonium iodide / tetrahydrofuran / 12 h / Heating

13: NBS / acetone; H₂O / -15 °C

14: 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 45 min, 2) reflux, 2h

15: 92 percent / ceriumtrichloride heptahydrate, NaBH₄ / ethanol / -15 °C

16: 56 percent / 1) p-toluenesulfonic acid monohydrate, 2) LiBH₄ / tetrahydrofuran / 1) reflux, 45 min, 2) r.t., 2h

17: 82.3 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

18: 88.5 percent / 1) trifluoromethanesulfonic acid, 2) LiAlH₄ / cyclohexane / 1) 12h, 2) 2h, r.t.

19: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

20: 92 percent / thiophenol, n-BuLi / tetrahydrofuran / -78 °C

21: 81 percent / 1) borane-dimethyl sulfide, dimethyl sulfide 2) NaOH, 30percent H₂O₂ / tetrahydrofuran / 1) 3h, r.t., 2) 2h, r.t.

22: 58 percent / 1) pyridinium p-toluenesulfonate, 2) diisobutylaluminum / benzene; CH₂Cl₂ / 1) reflux, 2h, 2) r.t. 1.5h

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; cerium(III) chloride; dimethylsulfide; trifluorormethanesulfonic acid; dimethylsulfide borane complex; Pd/Al; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Diisobutylaluminium hydride(1 M solution in tetrahydrofuran, 4.9 mL, 4.9 mmol); sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; thiophenol; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; cyclohexane; water; dimethyl sulfoxide; ethyl acetate; acetone; benzene;
DOI:10.1021/jo00292a045

Reference yield:

: 124095-53-0
Methyl 2,4-Dideoxy-2,4-dimethyl-α-L-xylopyranoside (Pyran 6)

: 123992-27-8
<2S-(2R*,3R*,4R*,5R*,6S*,8R*,9R+,10S*,11S*,12R*)>-13-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-2,4,6,8,10,12-hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1-tridecanol (Alcohol 36)

Guidance literature:: Multi-step reaction with 20 steps

1: 64 percent / TiCl₄ / CH₂Cl₂ / 1) 0 deg C, 2) r.t., 1.5h

2: 88 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

3: 100 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 8 h / Heating

4: NBS, NaHCO₃ / acetone; H₂O / -15 °C

5: 40 percent / 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 40 min, 2) reflux, 1h

6: 86 percent / cerium trichloride heptahydrate, NaBH₄ / ethanol / -15 °C

7: 91 percent / p-toluenesulfonic acid monohydrate / 2 h / Ambient temperature

8: 80 percent / H₂, 5percent Pd/Al / ethyl acetate / 36 h

9: 69 percent / TiCl₄ / CH₂Cl₂ / -78 °C

10: 94 percent / 95percent NaH, tetrabutylammonium iodide / tetrahydrofuran / 12 h / Heating

11: NBS / acetone; H₂O / -15 °C

12: 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 45 min, 2) reflux, 2h

13: 92 percent / ceriumtrichloride heptahydrate, NaBH₄ / ethanol / -15 °C

14: 56 percent / 1) p-toluenesulfonic acid monohydrate, 2) LiBH₄ / tetrahydrofuran / 1) reflux, 45 min, 2) r.t., 2h

15: 82.3 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

16: 88.5 percent / 1) trifluoromethanesulfonic acid, 2) LiAlH₄ / cyclohexane / 1) 12h, 2) 2h, r.t.

17: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

18: 92 percent / thiophenol, n-BuLi / tetrahydrofuran / -78 °C

19: 81 percent / 1) borane-dimethyl sulfide, dimethyl sulfide 2) NaOH, 30percent H₂O₂ / tetrahydrofuran / 1) 3h, r.t., 2) 2h, r.t.

20: 58 percent / 1) pyridinium p-toluenesulfonate, 2) diisobutylaluminum / benzene; CH₂Cl₂ / 1) reflux, 2h, 2) r.t. 1.5h

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; cerium(III) chloride; dimethylsulfide; trifluorormethanesulfonic acid; dimethylsulfide borane complex; Pd/Al; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Diisobutylaluminium hydride(1 M solution in tetrahydrofuran, 4.9 mL, 4.9 mmol); sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; thiophenol; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; cyclohexane; water; ethyl acetate; acetone; benzene;
DOI:10.1021/jo00292a045