(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester

Base Information

Chemical Name:(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester
CAS No.:371785-07-8
Molecular Formula:C₃₉H₇₀O₆Si₂
Molecular Weight:691.152
Hs Code.:

(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester

Synonyms:(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester

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Chemical Property of (3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester

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Technology Process of (3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester

There total 17 articles about (3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester 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:

: 371784-89-3
(S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-pentanol

: 371785-07-8
(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 93 percent / PPh₃; imidazole; I₂ / 4-DMAP / acetonitrile; diethyl ether / 1 h / 25 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 72 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 2.5 h / -78 - -30 °C

3.1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 25 °C

4.1: 95 percent / NaBH₄; NiCl₂; H₂ / ethylene diamine / ethanol / 1 h / 0 °C / 760.05 Torr

5.1: 99 percent / Et₂Zn; DME; cyclo-(S,S)-(n-Bu)B-[OCH(CONMe₂)]2 / CH₂Cl₂ / 6 h / 20 °C

6.1: Ag₂O; TBAI / toluene / 24 h / 25 - 50 °C

7.1: 499 mg / TBAF / tetrahydrofuran / 4 h / 25 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 25 °C

9.1: LDA / tetrahydrofuran / -78 - -40 °C

9.2: 1.14 g / tetrahydrofuran / 0.07 h / -78 °C

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 - 25 °C

11.1: HF*Py / pyridine; tetrahydrofuran / 2 h / 25 °C

12.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 6 h / 25 °C

13.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O; hexane / 0.17 h / 25 °C

14.1: 1.03 g / methanol; benzene; hexane

With 1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; 1,2-dimethoxyethane; 2-methyl-but-2-ene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; iodine; diethylzinc; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triphenylphosphine; nickel dichloride; silver(l) oxide; (4S,5S)-2-butyl-N⁴,N⁴,N⁵,N⁵-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide; lithium diisopropyl amide; dmap; ethylenediamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; benzene; 5.1: Charette cyclopropanation;
DOI:10.1021/ja011338b

Reference yield:

: 371784-87-1
(Z)-(S)-5-Benzyloxy-2-methyl-pent-3-en-1-ol

: 371785-07-8
(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 89 percent / imidazole / dimethylformamide / 1 h / 25 °C

2.1: 75 percent / H₂ / Pd/C / methanol; tetrahydrofuran / 10 h / 50 °C / 760.05 Torr

3.1: 93 percent / PPh₃; imidazole; I₂ / 4-DMAP / acetonitrile; diethyl ether / 1 h / 25 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 72 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 2.5 h / -78 - -30 °C

5.1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 25 °C

6.1: 95 percent / NaBH₄; NiCl₂; H₂ / ethylene diamine / ethanol / 1 h / 0 °C / 760.05 Torr

7.1: 99 percent / Et₂Zn; DME; cyclo-(S,S)-(n-Bu)B-[OCH(CONMe₂)]2 / CH₂Cl₂ / 6 h / 20 °C

8.1: Ag₂O; TBAI / toluene / 24 h / 25 - 50 °C

9.1: 499 mg / TBAF / tetrahydrofuran / 4 h / 25 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 25 °C

11.1: LDA / tetrahydrofuran / -78 - -40 °C

11.2: 1.14 g / tetrahydrofuran / 0.07 h / -78 °C

12.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 - 25 °C

13.1: HF*Py / pyridine; tetrahydrofuran / 2 h / 25 °C

14.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 6 h / 25 °C

15.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O; hexane / 0.17 h / 25 °C

16.1: 1.03 g / methanol; benzene; hexane

With 1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; 1,2-dimethoxyethane; 2-methyl-but-2-ene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; iodine; diethylzinc; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triphenylphosphine; nickel dichloride; silver(l) oxide; (4S,5S)-2-butyl-N⁴,N⁴,N⁵,N⁵-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide; lithium diisopropyl amide; dmap; palladium on activated charcoal; ethylenediamine; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 7.1: Charette cyclopropanation;
DOI:10.1021/ja011338b

Reference yield:

: 371784-90-6
tert-butyl-(5-iodo-2-methyl-pentyloxy)-diphenyl-silane

: 371785-07-8
(3S,6R,7S,8S)-11-((1R,2R)-2-Benzyloxymethyl-cyclopropyl)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-5-oxo-undecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 72 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 2.5 h / -78 - -30 °C

2.1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / 25 °C

3.1: 95 percent / NaBH₄; NiCl₂; H₂ / ethylene diamine / ethanol / 1 h / 0 °C / 760.05 Torr

4.1: 99 percent / Et₂Zn; DME; cyclo-(S,S)-(n-Bu)B-[OCH(CONMe₂)]2 / CH₂Cl₂ / 6 h / 20 °C

5.1: Ag₂O; TBAI / toluene / 24 h / 25 - 50 °C

6.1: 499 mg / TBAF / tetrahydrofuran / 4 h / 25 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 25 °C

8.1: LDA / tetrahydrofuran / -78 - -40 °C

8.2: 1.14 g / tetrahydrofuran / 0.07 h / -78 °C

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 - 25 °C

10.1: HF*Py / pyridine; tetrahydrofuran / 2 h / 25 °C

11.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 6 h / 25 °C

12.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O; hexane / 0.17 h / 25 °C

13.1: 1.03 g / methanol; benzene; hexane

With 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; 1,2-dimethoxyethane; 2-methyl-but-2-ene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; diethylzinc; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; nickel dichloride; silver(l) oxide; (4S,5S)-2-butyl-N⁴,N⁴,N⁵,N⁵-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide; lithium diisopropyl amide; ethylenediamine; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; water; toluene; tert-butyl alcohol; benzene; 4.1: Charette cyclopropanation;
DOI:10.1021/ja011338b