2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Base Information

Chemical Name:2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol
CAS No.:131310-63-9
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

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Chemical Property of 2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

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Technology Process of 2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

There total 13 articles about 2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol 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: 73.0%

: 131310-64-0
[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetaldehyde

: 131310-63-9
2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃;
DOI:10.1016/S0040-4039(99)01861-4

Reference yield:

: 22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7
2-deoxy-D-ribose

: 131310-63-9
2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Guidance literature:: Multi-step reaction with 11 steps

1: 97 percent / tetrahydrofuran / 3 h / Heating

2: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

3: 98 percent / imidazole / dimethylformamide / 5 h / 25 °C

4: 98 percent / DIBAL / CH₂Cl₂ / 0.67 h / -78 °C

5: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -27 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

6: 94 percent / SO₃*pyridine, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 3.5 h / 0 °C

7: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.25 h / 0 °C

8: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

9: 86 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 0 °C

10: 97 percent / imidazole / dimethylformamide / 10.5 h / 50 °C

11: 1.) 9-BBN, 2.) NaOH, hydrogen peroxide / 1.) THF, 25 deg C, 40 min, 2.) 30 min.

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 131310-63-9
2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

Guidance literature:: Multi-step reaction with 10 steps

1: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

2: 98 percent / imidazole / dimethylformamide / 5 h / 25 °C

3: 98 percent / DIBAL / CH₂Cl₂ / 0.67 h / -78 °C

4: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -27 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

5: 94 percent / SO₃*pyridine, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 3.5 h / 0 °C

6: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.25 h / 0 °C

7: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

8: 86 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 0 °C

9: 97 percent / imidazole / dimethylformamide / 10.5 h / 50 °C

10: 1.) 9-BBN, 2.) NaOH, hydrogen peroxide / 1.) THF, 25 deg C, 40 min, 2.) 30 min.

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)85579-4