(E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol

Base Information

Chemical Name:(E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol
CAS No.:168777-86-4
Molecular Formula:C₇₀H₁₀₈O₁₀Si₂
Molecular Weight:1165.79
Hs Code.:

(E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol

Synonyms:(E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol

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Chemical Property of (E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol

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Technology Process of (E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol

There total 47 articles about (E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-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: 98.0%

: 148933-74-8
C₈₀H₁₁₅NO₁₂Si₂

: 168777-86-4
(E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol

Guidance literature:: With lithium borohydride; In diethyl ether; water; at 0 ℃; for 1h;
DOI:10.1039/c39930000619

Reference yield:

: 128209-97-2
(1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde

: 168777-86-4
(E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / LiCl, (i-Pr)2NEt / acetonitrile / 1.) 25 deg C, 15 min, 2.) 25 deg C, 6 h

2: Et₃SiH / Rh(PPh₃)3Cl / 2 h / 50 °C

3: 49percent aq. HF / acetonitrile / 3 h / 25 °C

4: imidazole / dimethylformamide / 16 h / 25 °C

6: 98 percent / aq. LiBH₄ / diethyl ether; tetrahydrofuran / 1 h / 25 °C

With 1H-imidazole; triethylsilane; lithium borohydride; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; lithium chloride; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 148933-83-9
(1R,2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexanol

: 168777-86-4
(E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) r.t., 2 h

2: LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) 25 deg C, 2 h

3: Pd(OAc)2 / acetonitrile / 24 h / 50 °C

4: 95 percent / LiBH₄, CeCl₃*7H₂O / tetrahydrofuran; methanol / 1 h / -78 °C

5: 2.) LiEt₃BH / 1.) xylene, reflux, 48 h, 2.) THF, r.t., 2 h

6: 100 percent / H₂ / 10percent Pd/C / ethanol / 16 h / 25 °C

7: 1.) o-O₂NC₆H₄SeCN, n-Bu₃P, 2.) 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 3 h, 2.) THF, 25 deg C, 6 h

8: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) 25 deg C, overnight

9: 95 percent / LiCl, (i-Pr)2NEt / acetonitrile / 1.) 25 deg C, 15 min, 2.) 25 deg C, 6 h

10: Et₃SiH / Rh(PPh₃)3Cl / 2 h / 50 °C

11: 49percent aq. HF / acetonitrile / 3 h / 25 °C

12: imidazole / dimethylformamide / 16 h / 25 °C

14: 98 percent / aq. LiBH₄ / diethyl ether; tetrahydrofuran / 1 h / 25 °C

With 1H-imidazole; triethylsilane; palladium diacetate; lithium borohydride; ortho-nitrophenyl selenocyanate; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; tributylphosphine; hydrogen fluoride; hydrogen; dihydrogen peroxide; lithium triethylborohydride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; Wilkinson's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; acetonitrile;