1-<(tert-butyldiphenylsilyl)oxy>-2(R),4(R),6(S),9-tetramethyldec-7(E)-ene-3(R),5(R)-diol

Base Information

Chemical Name:1-<(tert-butyldiphenylsilyl)oxy>-2(R),4(R),6(S),9-tetramethyldec-7(E)-ene-3(R),5(R)-diol
CAS No.:122292-23-3
Molecular Formula:C₃₀H₄₆O₃Si
Molecular Weight:482.779
Hs Code.:

Synonyms:1-<(tert-butyldiphenylsilyl)oxy>-2(R),4(R),6(S),9-tetramethyldec-7(E)-ene-3(R),5(R)-diol

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Chemical Property of 1-<(tert-butyldiphenylsilyl)oxy>-2(R),4(R),6(S),9-tetramethyldec-7(E)-ene-3(R),5(R)-diol

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Technology Process of 1-<(tert-butyldiphenylsilyl)oxy>-2(R),4(R),6(S),9-tetramethyldec-7(E)-ene-3(R),5(R)-diol

There total 9 articles about 1-<(tert-butyldiphenylsilyl)oxy>-2(R),4(R),6(S),9-tetramethyldec-7(E)-ene-3(R),5(R)-diol 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: 92.0%

: 112452-63-8,122292-22-2
Acetic acid (E)-(1R,2R,3R,4S)-3-acetoxy-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,4,7-trimethyl-oct-5-enyl ester

: 122292-23-3
1-<(tert-butyldiphenylsilyl)oxy>-2(R),4(R),6(S),9-tetramethyldec-7(E)-ene-3(R),5(R)-diol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/jo00275a019

Reference yield:

: 110455-56-6
3(S)-(1(S),4-dimethyl-2(E)-pentenyl)-4(S)-methyl-5(R)-<1(S)-methyl-2<(tert-butyldiphenylsilyl)oxy>ethyl>dihydro-2(3H)-furanone

: 115047-25-1,122292-23-3,126720-99-8
(E)-(2S,3S,4S,5S,6S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4,6,9-tetramethyl-dec-7-ene-3,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1: diethyl ether / 15 h / -18 °C

2: H₂O₂, HOAc / tetrahydrofuran / 0 deg C, 30 min, 25 deg C, 16 h

3: 1.)triethylamine, 4-(dimethylamino)pyridine, acetic anhydride, 2.) diisobutylaluminum hydride / 1.) CH₂Cl₂, 0 deg C, 30 min, 25 deg C, 1 h, reflux, 6 h, 2.) CH₂Sl₂, -78 deg C, 2 h

With dmap; dihydrogen peroxide; acetic anhydride; diisobutylaluminium hydride; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja00224a032

Reference yield:

: 103576-61-0
4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-dihydro-2(3H)furanone

: 115047-25-1,122292-23-3,126720-99-8
(E)-(2S,3S,4S,5S,6S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4,6,9-tetramethyl-dec-7-ene-3,5-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 3 h

2: 1.) NaH, 2.) (Ph₃P)4Pd, Ph₃P / 1.) THF, 25 deg C, 2.) THF, 0 deg C, 1 h, 25 deg C, 2 h

3: 71 percent / LiCl / H₂O; dimethylsulfoxide / 3 h / 200 °C

4: diethyl ether / 15 h / -18 °C

5: H₂O₂, HOAc / tetrahydrofuran / 0 deg C, 30 min, 25 deg C, 16 h

6: 1.)triethylamine, 4-(dimethylamino)pyridine, acetic anhydride, 2.) diisobutylaluminum hydride / 1.) CH₂Cl₂, 0 deg C, 30 min, 25 deg C, 1 h, reflux, 6 h, 2.) CH₂Sl₂, -78 deg C, 2 h

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dihydrogen peroxide; acetic anhydride; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; water; dimethyl sulfoxide;
DOI:10.1021/ja00224a032