(3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol

Base Information

Chemical Name:(3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol
CAS No.:869732-17-2
Molecular Formula:C₂₅H₃₃BrO₄
Molecular Weight:477.439
Hs Code.:

Synonyms:(3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol

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Chemical Property of (3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol

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Technology Process of (3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol

There total 12 articles about (3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol 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:

: 869732-13-8
3-(benzyloxy)-5-bromo-2-methoxybenzaldehyde

: 869732-17-2
(3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 64 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 18 h / -50 °C

2.1: 60 percent / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / 8 h / 20 °C

3.1: BH₃*Me₂S / tetrahydrofuran / 18 h / 0 - 20 °C

3.2: 62 percent / H₂O₂; aq. NaOH / tetrahydrofuran; methanol / 2.5 h / 0 - 20 °C

4.1: 97 percent / 1H-imidazole / dimethylformamide; diethyl ether / 4 h / 0 °C

5.1: 99 percent / N,N,N',N'-tetramethyl-1,8-naphthalenediamine; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

6.1: 99 percent / HCl / methanol / 1 h / 20 °C

7.1: 90 percent / BCl₃*Me₂S / CH₂Cl₂ / 5 h / -78 - 0 °C

8.1: aq. NaIO₄; NaHCO₃ / acetone / 2 h / 20 °C

9.1: 80 percent / 4 Angstroem molecular sieves / toluene / 16 h / -78 °C

With 1H-imidazole; hydrogenchloride; triethylsilane; sodium periodate; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; boron trichloride - methyl sulfide complex; 4 A molecular sieve; boron trifluoride diethyl etherate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja055384d

Reference yield:

: 869732-27-4
(2R,3S,5R)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol

: 869732-17-2
(3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol

Guidance literature:: Multi-step reaction with 2 steps

1: aq. NaIO₄; NaHCO₃ / acetone / 2 h / 20 °C

2: 80 percent / 4 Angstroem molecular sieves / toluene / 16 h / -78 °C

With sodium periodate; 4 A molecular sieve; sodium hydrogencarbonate; In acetone; toluene;
DOI:10.1021/ja055384d

Reference yield:

: 869732-23-0
(E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

: 869732-17-2
(3S,4R,5S,7R)-8-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methoxy-3,7-dimethyloct-1-en-4-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: BH₃*Me₂S / tetrahydrofuran / 18 h / 0 - 20 °C

1.2: 62 percent / H₂O₂; aq. NaOH / tetrahydrofuran; methanol / 2.5 h / 0 - 20 °C

2.1: 97 percent / 1H-imidazole / dimethylformamide; diethyl ether / 4 h / 0 °C

3.1: 99 percent / N,N,N',N'-tetramethyl-1,8-naphthalenediamine; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 20 °C

4.1: 99 percent / HCl / methanol / 1 h / 20 °C

5.1: 90 percent / BCl₃*Me₂S / CH₂Cl₂ / 5 h / -78 - 0 °C

6.1: aq. NaIO₄; NaHCO₃ / acetone / 2 h / 20 °C

7.1: 80 percent / 4 Angstroem molecular sieves / toluene / 16 h / -78 °C

With 1H-imidazole; hydrogenchloride; sodium periodate; dimethylsulfide borane complex; boron trichloride - methyl sulfide complex; 4 A molecular sieve; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja055384d