<2S-<2α(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13)

Base Information

• Chemical Name: <2S-<2α(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13)
• CAS No.: 123992-13-2
• Molecular Formula: C₃₉H₅₄O₄Si
• Molecular Weight: 614.941
• Mol file: 123992-13-2.mol

Synonyms:<2S-<2α(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13)

Chemical Property of <2S-<2α(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2S-<2α(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13)

There total 11 articles about <2S-<2α(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13) 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: 91.0%

1,5-Anhydro-2,4,6,8-tetradeoxy-9-O-<(1,1-dimethylethyl)-diphenylsilyl>-2,4,6,8-tetramethyl-7-O-(phenylmethyl)-L-threo-L-galacto-non-1-enitol (Pyran 12) (123992-12-1) + isopropyl alcohol (67-63-0,8013-70-5) → <2S-<2α(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13) (123992-13-2)

Guidance literature:

With toluene-4-sulfonic acid; for 2h; Ambient temperature;

DOI:10.1021/jo00292a045

Reference yield:

2,3-Dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 4) (36019-62-2) → <2S-<2α(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13) (123992-13-2)

Guidance literature:

Multi-step reaction with 9 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

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; 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; 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(2R*,3S*,4R*),3β,6β>>-<<4-<3,6-Dihydro-3,5-dimethyl-6-(1-methylethoxy)-2H-pyran-2-yl>-2-methyl-3-(phenylmethoxy)pentyl>oxy>(1,1-dimethylethyl)diphenylsilane (Pyran 13) (123992-13-2)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/jo00292a045

upstream raw materials:

1,5-Anhydro-2,4,6,8-tetradeoxy-9-O-<(1,1-dimethylethyl)-diphenylsilyl>-2,4,6,8-tetramethyl-7-O-(phenylmethyl)-L-threo-L-galacto-non-1-enitol (Pyran 12)

isopropyl alcohol

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

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

Downstream raw materials:

<2S-<2α(2R*,3S*,4R*),3β,5β,6β>>-(1,1-Dimethylethyl)<<2-methyl-3-(phenylmethoxy)-4-pentyl>oxy>diphenylsilane (Pyran 14)

<αS-<αR*(1S*,2S*,3R*),βR*,δS*>>-α-<4-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-1,3-dimethyl-2-(phenylmethoxy)-butyl>-β,δ-dimethyl-1,3-dithiane-2-butanol (Dithiane-Alcohol 15)

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

<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)