(1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate

Base Information

Chemical Name:(1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate
CAS No.:930285-73-7
Molecular Formula:C₅₃H₈₆O₉Si₂
Molecular Weight:923.431
Hs Code.:

(1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate

Synonyms:(1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate

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Chemical Property of (1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate

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Technology Process of (1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate

There total 29 articles about (1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate 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:

: 930285-77-1
2-allyl-4,6-dimethoxybenzoic acid

: 930285-73-7
(1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 14.45 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 20 °C

2.1: 4-methylmorpholine N-oxide; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C

3.1: 6.3 g / NaIO₄ / methanol; H₂O / 2 h / 20 °C

4.1: nBu₂BOTf / toluene; CH₂Cl₂ / 0.08 h / -10 °C

4.2: iPr₂NEt / toluene; CH₂Cl₂ / 2 h / 0 °C

4.3: 85 percent / toluene; CH₂Cl₂ / -78 - 0 °C

5.1: 95 percent / proton sponge / CH₂Cl₂ / -60 - 20 °C

6.1: 94 percent / NaBH₄ / tetrahydrofuran; H₂O / 73 h / 0 - 20 °C

7.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

8.1: 97 percent / sodium iodide; zinc / 1,2-dimethoxy-ethane / 4 h / Heating

9.1: 95 percent / KOH / ethanol; H₂O / 20 h / Heating

10.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.2: 98 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

11.1: dimethylformamide / 4 h / 50 °C

12.1: sodium hydride / dimethylformamide / 0 - 20 °C

13.1: 0.485 g / 2,6-lutidine / CH₂Cl₂ / -50 - 20 °C

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; Proton Sponge; di-n-butylboryl trifluoromethanesulfonate; water; sodium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; zinc; osmium(VIII) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4.3: Evans aldol reaction;
DOI:10.1021/ol0629317

Reference yield:

: 91-52-1
2,4 dimethoxybenzoic acid

: 930285-73-7
(1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate

Guidance literature:: Multi-step reaction with 14 steps

1.1: sBuLi; TMEDA / tetrahydrofuran; cyclohexane / 1.5 h / -90 - -78 °C

1.2: tetrahydrofuran; cyclohexane / 1.5 h / cooling

2.1: 14.45 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 24 h / 20 °C

3.1: 4-methylmorpholine N-oxide; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C

4.1: 6.3 g / NaIO₄ / methanol; H₂O / 2 h / 20 °C

5.1: nBu₂BOTf / toluene; CH₂Cl₂ / 0.08 h / -10 °C

5.2: iPr₂NEt / toluene; CH₂Cl₂ / 2 h / 0 °C

5.3: 85 percent / toluene; CH₂Cl₂ / -78 - 0 °C

6.1: 95 percent / proton sponge / CH₂Cl₂ / -60 - 20 °C

7.1: 94 percent / NaBH₄ / tetrahydrofuran; H₂O / 73 h / 0 - 20 °C

8.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

9.1: 97 percent / sodium iodide; zinc / 1,2-dimethoxy-ethane / 4 h / Heating

10.1: 95 percent / KOH / ethanol; H₂O / 20 h / Heating

11.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C

11.2: 98 percent / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

12.1: dimethylformamide / 4 h / 50 °C

13.1: sodium hydride / dimethylformamide / 0 - 20 °C

14.1: 0.485 g / 2,6-lutidine / CH₂Cl₂ / -50 - 20 °C

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium tetrahydroborate; sodium periodate; n-butyllithium; Proton Sponge; N,N,N,N,-tetramethylethylenediamine; di-n-butylboryl trifluoromethanesulfonate; water; sec.-butyllithium; sodium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; zinc; osmium(VIII) oxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 5.3: Evans aldol reaction;
DOI:10.1021/ol0629317

Reference yield:

: 71565-21-4
(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol

: 930285-73-7
(1S)-1-{(1R,2R,3R)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-[(3,4-dimethoxybenzyl)oxy]-1,3-dimethylpentyl}pent-3-ynyl 2,4-dimethoxy-6-{(2R,3S)-3-methyl-2-[(triisopropylsilyl)oxy]hept-5-ynyl}benzoate

Guidance literature:: Multi-step reaction with 16 steps

1.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 4.5 h / -78 - 20 °C

2.1: diethylzinc / Pd(OAc)2; PPh₃ / tetrahydrofuran; hexane / 72 h / -20 °C

3.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -50 - 20 °C

4.1: 1,2-dimethoxy-ethane / 3.08 h / 0 - 20 °C

5.1: 3.11 g / H₂O₂; NaOH / 1,2-dimethoxy-ethane; H₂O / 0.42 h / 0 - 20 °C

6.1: 95 percent / sodium borohydride / tetrahydrofuran; methanol / 1 h / 0 °C

7.1: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 72 h

8.1: 96 percent / CuCl₂*2H₂O / acetonitrile / 20 h / -5 °C

9.1: 96 percent / NaH; N-(2,4,6-triisopropylbenzenesulfonyl)imidazole / tetrahydrofuran / 0 - 20 °C

10.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.2: BF₃*OEt₂ / tetrahydrofuran; hexane / 0.83 h / -78 °C

10.3: 83 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C

11.1: 99 percent / K₂CO₃; methanol / 3 h / 20 °C

12.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -50 - 20 °C

13.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C

13.2: 99 percent / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

14.1: 99 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

15.1: sodium hydride / dimethylformamide / 0 - 20 °C

16.1: 0.485 g / 2,6-lutidine / CH₂Cl₂ / -50 - 20 °C

With 2,6-dimethylpyridine; methanol; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; diethylzinc; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole; palladium diacetate; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Swern oxidation / 2.1: Marshall reaction;
DOI:10.1021/ol0629317