<2S-<2α(1S*,3R*,4R*,5S*,6S*,7R*),3>>-2-<8-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3,5,7-tetramethyl-4,6-bis-(phenylmethoxy)octyl>-2,3-dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 19)

Base Information

• Chemical Name: <2S-<2α(1S*,3R*,4R*,5S*,6S*,7R*),3>>-2-<8-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3,5,7-tetramethyl-4,6-bis-(phenylmethoxy)octyl>-2,3-dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 19)
• CAS No.: 124095-54-1
• Molecular Formula: C₄₉H₆₄O₅Si
• Molecular Weight: 761.13
• Mol file: 124095-54-1.mol

Synonyms:

Chemical Property of <2S-<2α(1S*,3R*,4R*,5S*,6S*,7R*),3>>-2-<8-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3,5,7-tetramethyl-4,6-bis-(phenylmethoxy)octyl>-2,3-dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 19)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2S-<2α(1S*,3R*,4R*,5S*,6S*,7R*),3>>-2-<8-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3,5,7-tetramethyl-4,6-bis-(phenylmethoxy)octyl>-2,3-dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 19)

There total 16 articles about <2S-<2α(1S*,3R*,4R*,5S*,6S*,7R*),3>>-2-<8-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3,5,7-tetramethyl-4,6-bis-(phenylmethoxy)octyl>-2,3-dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 19) 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:

2,3-Dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 4) (36019-62-2) → <2S-<2α(1S*,3R*,4R*,5S*,6S*,7R*),3>>-2-<8-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3,5,7-tetramethyl-4,6-bis-(phenylmethoxy)octyl>-2,3-dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 19) (124095-54-1)

Guidance literature:

Multi-step reaction with 14 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

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; 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; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; 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-<2α(1S*,3R*,4R*,5S*,6S*,7R*),3>>-2-<8-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3,5,7-tetramethyl-4,6-bis-(phenylmethoxy)octyl>-2,3-dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 19) (124095-54-1)

Guidance literature:

Multi-step reaction with 12 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

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

DOI:10.1021/jo00292a045

Reference yield:

cis/trans-(+/-)-5,6-Dihydro-2-methoxy-3,5-dimethyl-2H-pyran (Pyran 5) (123992-05-2,123992-06-3) → <2S-<2α(1S*,3R*,4R*,5S*,6S*,7R*),3>>-2-<8-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3,5,7-tetramethyl-4,6-bis-(phenylmethoxy)octyl>-2,3-dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 19) (124095-54-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 80 percent / borane-dimethyl sulfide complex, NaOH, 30percent H₂O₂ / tetrahydrofuran; dimethylsulfoxide / 4 h

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

3: 88 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

4: 100 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 8 h / Heating

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

6: 40 percent / 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 40 min, 2) reflux, 1h

7: 86 percent / cerium trichloride heptahydrate, NaBH₄ / ethanol / -15 °C

8: 91 percent / p-toluenesulfonic acid monohydrate / 2 h / Ambient temperature

9: 80 percent / H₂, 5percent Pd/Al / ethyl acetate / 36 h

10: 69 percent / TiCl₄ / CH₂Cl₂ / -78 °C

11: 94 percent / 95percent NaH, tetrabutylammonium iodide / tetrahydrofuran / 12 h / Heating

12: NBS / acetone; H₂O / -15 °C

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

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; 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; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetone; benzene;

DOI:10.1021/jo00292a045

upstream raw materials:

(E,Z)-3-<(tert-butyldimethylsilyl)oxy>-1-methoxy-2-methyl-1,3-pentadiene

(2R,4S,5S,6R,7R,8S)-5,7-Bis-benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-2,4,6,8-tetramethyl-nonanal

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

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