(2R,4R,5S,6S,7R)-9-(Benzyloxy)-4-(cyanomethyl)-5,7-(isopropylidenedioxy)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethylnonane

Base Information

Chemical Name:(2R,4R,5S,6S,7R)-9-(Benzyloxy)-4-(cyanomethyl)-5,7-(isopropylidenedioxy)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethylnonane
CAS No.:138152-92-8
Molecular Formula:C₃₂H₄₅NO₆
Molecular Weight:539.712
Hs Code.:

Synonyms:(2R,4R,5S,6S,7R)-9-(Benzyloxy)-4-(cyanomethyl)-5,7-(isopropylidenedioxy)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethylnonane

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Chemical Property of (2R,4R,5S,6S,7R)-9-(Benzyloxy)-4-(cyanomethyl)-5,7-(isopropylidenedioxy)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethylnonane

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Technology Process of (2R,4R,5S,6S,7R)-9-(Benzyloxy)-4-(cyanomethyl)-5,7-(isopropylidenedioxy)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethylnonane

There total 34 articles about (2R,4R,5S,6S,7R)-9-(Benzyloxy)-4-(cyanomethyl)-5,7-(isopropylidenedioxy)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethylnonane 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:

: 19790-60-4
3-Benzyloxypropanal

: 138152-92-8
(2R,4R,5S,6S,7R)-9-(Benzyloxy)-4-(cyanomethyl)-5,7-(isopropylidenedioxy)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethylnonane

Guidance literature:: Multi-step reaction with 15 steps

1: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 15 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> 0 deg C, 19 h

2: DIBAH / CH₂Cl₂ / 1 h / -78 °C

3: L-(+)-diethyl tartrate, titanium isopropoxide, 3-Angstroem molecular sieves, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / -15 °C

4: oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

5: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 10 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> rt

6: 79 percent / DIBAH / diethyl ether; hexane / 0.25 h / -78 °C

8: 93 percent / NEt₃, DMAP / CH₂Cl₂ / Ambient temperature

9: 37 percent / magnesium monoperoxyphthalic acid / propan-2-ol; H₂O / 20 h / Ambient temperature

10: 89 percent / LiNEt₂ / diethyl ether; hexane / 52 h / 0 °C

11: 89 percent / pyridinium p-toluenesulfonate / 62 h / 35 °C

12: 80 percent / H₂ / PtO₂ / ethanol / 1 h / Ambient temperature

13: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5.5 h / Ambient temperature

14: 98 percent / NEt₃ / CH₂Cl₂ / 1) 0 deg C, 5 h, 2) rt, 2 h

15: 83 percent / dimethylformamide / 42.5 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 3 A molecular sieve; lithium diethylamide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; magnesium monoperoxyphthalate hexahydrate; dimethyl sulfoxide; triethylamine; platinum(IV) oxide; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo00027a022

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 138152-92-8,138284-08-9
(3R,5R)-3-[(4R,5R,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-6-(4-methoxy-benzyloxymethoxy)-5-methyl-hexanenitrile

Guidance literature:: Multi-step reaction with 15 steps

1: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 15 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> 0 deg C, 19 h

2: DIBAH / CH₂Cl₂ / 1 h / -78 °C

3: L-(+)-diethyl tartrate, titanium isopropoxide, 3-Angstroem molecular sieves, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / -15 °C

4: oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

5: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 10 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> rt

6: 79 percent / DIBAH / diethyl ether; hexane / 0.25 h / -78 °C

8: 93 percent / NEt₃, DMAP / CH₂Cl₂ / Ambient temperature

9: 43 percent / magnesium monoperoxyphthalic acid / propan-2-ol; H₂O / 20 h / Ambient temperature

10: 89 percent / LiNEt₂ / diethyl ether / 0 °C

11: pyridinium p-toluenesulfonate / 35 °C

12: H₂ / PtO₂ / ethanol / Ambient temperature

13: tetrabutylammonium fluoride / tetrahydrofuran / 5.5 h / Ambient temperature

14: NEt₃ / CH₂Cl₂ / 1) 0 deg C, 5 h, 2) rt, 2 h

15: dimethylformamide / 42.5 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 3 A molecular sieve; lithium diethylamide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; magnesium monoperoxyphthalate hexahydrate; dimethyl sulfoxide; triethylamine; platinum(IV) oxide; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo00027a022

Reference yield:

: 4799-68-2
3-benzyloxypropan-1-ol

: 138152-92-8
(2R,4R,5S,6S,7R)-9-(Benzyloxy)-4-(cyanomethyl)-5,7-(isopropylidenedioxy)-1-<<(p-methoxybenzyl)oxy>methoxy>-2,6-dimethylnonane

Guidance literature:: Multi-step reaction with 16 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -78 °C

2: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 15 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> 0 deg C, 19 h

3: DIBAH / CH₂Cl₂ / 1 h / -78 °C

4: L-(+)-diethyl tartrate, titanium isopropoxide, 3-Angstroem molecular sieves, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / -15 °C

5: oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

6: 1) KHMDS, 18-crown-6 / 1) THF, toluene, -78 deg C, 10 min, 2) THF, -78 deg C, 45 min, then -78 deg C -> rt

7: 79 percent / DIBAH / diethyl ether; hexane / 0.25 h / -78 °C

9: 93 percent / NEt₃, DMAP / CH₂Cl₂ / Ambient temperature

10: 37 percent / magnesium monoperoxyphthalic acid / propan-2-ol; H₂O / 20 h / Ambient temperature

11: 89 percent / LiNEt₂ / diethyl ether; hexane / 52 h / 0 °C

12: 89 percent / pyridinium p-toluenesulfonate / 62 h / 35 °C

13: 80 percent / H₂ / PtO₂ / ethanol / 1 h / Ambient temperature

14: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 5.5 h / Ambient temperature

15: 98 percent / NEt₃ / CH₂Cl₂ / 1) 0 deg C, 5 h, 2) rt, 2 h

16: 83 percent / dimethylformamide / 42.5 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; oxalyl dichloride; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 3 A molecular sieve; lithium diethylamide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; magnesium monoperoxyphthalate hexahydrate; dimethyl sulfoxide; triethylamine; platinum(IV) oxide; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo00027a022