((1R,2S)-1-(2-Benzyloxy-ethyl)-2-{(2R,3R)-5-methoxy-3-[(R)-3-(4-methoxy-benzyloxymethoxy)-2-methyl-propyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-dimethyl-silane

Base Information

Chemical Name:((1R,2S)-1-(2-Benzyloxy-ethyl)-2-{(2R,3R)-5-methoxy-3-[(R)-3-(4-methoxy-benzyloxymethoxy)-2-methyl-propyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-dimethyl-silane
CAS No.:138152-94-0
Molecular Formula:C₃₆H₅₈O₇Si
Molecular Weight:630.938
Hs Code.:

((1R,2S)-1-(2-Benzyloxy-ethyl)-2-{(2R,3R)-5-methoxy-3-[(R)-3-(4-methoxy-benzyloxymethoxy)-2-methyl-propyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-dimethyl-silane

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Chemical Property of ((1R,2S)-1-(2-Benzyloxy-ethyl)-2-{(2R,3R)-5-methoxy-3-[(R)-3-(4-methoxy-benzyloxymethoxy)-2-methyl-propyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-dimethyl-silane

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Technology Process of ((1R,2S)-1-(2-Benzyloxy-ethyl)-2-{(2R,3R)-5-methoxy-3-[(R)-3-(4-methoxy-benzyloxymethoxy)-2-methyl-propyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-dimethyl-silane

There total 40 articles about ((1R,2S)-1-(2-Benzyloxy-ethyl)-2-{(2R,3R)-5-methoxy-3-[(R)-3-(4-methoxy-benzyloxymethoxy)-2-methyl-propyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-dimethyl-silane 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: 100.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 138152-93-9,138284-03-4,138284-09-0,138284-10-3
(2S,3R)-2-<(1R,2R)-4-(Benzyloxy)-2-hydroxy-1-methylbutyl>-3-<(2R)-3-<<(p-methoxybenzyl)oxy>methoxy>-2-methylpropyl>-5-methoxy-1,2,3,4-tetrahydrofuran

: 138152-94-0,138284-04-5,138284-11-4,138284-12-5
(2S,3R)-2-<(1R,2R)-4-(Benzyloxy)-2-<(tert-butyldimethylsilyl)oxy>-1-methylbutyl>-3-<(2R)-3-<<(p-methoxybenzyl)oxy>methoxy>-2-methylpropyl>-5-methoxy-1,2,3,4-tetrahydrofuran

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo00027a022

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 138152-94-0,138284-04-5,138284-11-4,138284-12-5
(2S,3R)-2-<(1R,2R)-4-(Benzyloxy)-2-<(tert-butyldimethylsilyl)oxy>-1-methylbutyl>-3-<(2R)-3-<<(p-methoxybenzyl)oxy>methoxy>-2-methylpropyl>-5-methoxy-1,2,3,4-tetrahydrofuran

Guidance literature:: Multi-step reaction with 18 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

16: DIBAH / diethyl ether; hexane / 1) 0 deg C, 30 min, 2) rt, 3 h

17: HCl / diethyl ether / 12 h / 0 °C

18: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; 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

: 138152-94-0,138284-04-5,138284-11-4,138284-12-5
((1R,2S)-1-(2-Benzyloxy-ethyl)-2-{(2R,3R)-5-methoxy-3-[(R)-3-(4-methoxy-benzyloxymethoxy)-2-methyl-propyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 18 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

16: DIBAH / diethyl ether; hexane / 1) 0 deg C, 30 min, 2) rt, 3 h

17: 91 percent / HCl / 0.08 h / 0 °C

18: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; 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