<2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40)

Base Information

• Chemical Name: <2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40)
• CAS No.: 123992-30-3
• Molecular Formula: C₄₉H₆₈O₆
• Molecular Weight: 753.075
• Mol file: 123992-30-3.mol

Synonyms:

Chemical Property of <2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40)

There total 22 articles about <2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40) 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: 31.0%

(3R,4S,5R,6S,7S,9R,10S,11S,12S,13S,14R)-4,6,10,12-Tetrakis-benzyloxy-14-ethyl-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one (123992-32-5) → <2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40) (123992-30-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 1h; Ambient temperature;

DOI:10.1021/jo00292a045

Reference yield:

2,3-Dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 4) (36019-62-2) → <2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40) (123992-30-3)

Guidance literature:

Multi-step reaction with 21 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: trifluoromethanesulfonic acid / cyclohexane / 48 h

21: 31 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium borohydride; cerium(III) chloride; 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; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; cyclohexane; water; dimethyl sulfoxide; ethyl acetate; acetone; benzene;

DOI:10.1021/jo00292a045

Reference yield:

Methyl 2,4-Dideoxy-2,4-dimethyl-α-L-xylopyranoside (Pyran 6) (124095-53-0) → <2S-(2R*,3S*,4S*,5R*,6R*,8S*,9R+,10R*,11R*,12R*,13S*)>-2,4,6,8,10,12-Hexamethyl-3,5,9,11-tetrakis(phenylmethoxy)-1,13-pentadecanediol (Diol 40) (123992-30-3)

Guidance literature:

Multi-step reaction with 19 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: trifluoromethanesulfonic acid / cyclohexane / 48 h

19: 31 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium borohydride; cerium(III) chloride; trifluorormethanesulfonic acid; Pd/Al; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; cyclohexane; water; ethyl acetate; acetone; benzene;

DOI:10.1021/jo00292a045

upstream raw materials:

(3R,4S,5R,6S,7S,9R,10S,11S,12S,13S,14R)-4,6,10,12-Tetrakis-benzyloxy-14-ethyl-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

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

Methyl 2,4-Dideoxy-2,4-dimethyl-α-L-xylopyranoside (Pyran 6)

cis/trans-(+/-)-5,6-Dihydro-2-methoxy-3,5-dimethyl-2H-pyran (Pyran 5)

Downstream raw materials:

<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

<5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41)