1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene

Base Information

Chemical Name:1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene
CAS No.:869732-31-0
Molecular Formula:C₂₇H₃₅BrO₅
Molecular Weight:519.476
Hs Code.:

Synonyms:1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene

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Chemical Property of 1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene

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Technology Process of 1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene

There total 17 articles about 1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene 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:

: 869732-30-9
(2R,3R,4S,6R)-7-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-4-methoxy-3-methoxymethoxy-2,6-dimethyl-heptanal

: 27491-70-9,28447-24-7,25411-73-8
dimethyl diazomethylphosphonate

: 869732-31-0
1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene

Guidance literature:: dimethyl diazomethylphosphonate; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 0.25h;

(2R,3R,4S,6R)-7-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-4-methoxy-3-methoxymethoxy-2,6-dimethyl-heptanal; In tetrahydrofuran; at -78 ℃; for 0.25h;
DOI:10.1021/ja055384d

Reference yield:

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

: 869732-31-0
1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene

Guidance literature:: Multi-step reaction with 13 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

10.1: 82 percent / DMAP; N,N-diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

11.1: OsO₄; N-methylmorpholine N-oxide / toluene; acetone; H₂O / 4 h / 20 °C

12.1: Pb(OAc)4; K₂CO₃ / benzene / 0.5 h

13.1: t-BuOK / tetrahydrofuran / 0.25 h / -78 °C

13.2: 0.050 g / tetrahydrofuran / 0.25 h / -78 °C

With 1H-imidazole; lead(IV) acetate; hydrogenchloride; triethylsilane; dmap; sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; boron trichloride - methyl sulfide complex; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/ja055384d

Reference yield:

: 869732-16-1
(2S,4R)-5-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-2-methoxy-4-methylpentanal

: 869732-31-0
1-Benzyloxy-5-bromo-2-methoxy-3-((2R,4S,5R,6S)-4-methoxy-5-methoxymethoxy-2,6-dimethyl-oct-7-ynyl)-benzene

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / 4 Angstroem molecular sieves / toluene / 16 h / -78 °C

2.1: 82 percent / DMAP; N,N-diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

3.1: OsO₄; N-methylmorpholine N-oxide / toluene; acetone; H₂O / 4 h / 20 °C

4.1: Pb(OAc)4; K₂CO₃ / benzene / 0.5 h

5.1: t-BuOK / tetrahydrofuran / 0.25 h / -78 °C

5.2: 0.050 g / tetrahydrofuran / 0.25 h / -78 °C

With lead(IV) acetate; dmap; osmium(VIII) oxide; 4 A molecular sieve; potassium tert-butylate; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; benzene;
DOI:10.1021/ja055384d