(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one

Base Information

Chemical Name:(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one
CAS No.:371785-00-1
Molecular Formula:C₄₄H₈₄O₅Si₃
Molecular Weight:777.404
Hs Code.:

Synonyms:(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one

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Chemical Property of (3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one

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Technology Process of (3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one

There total 18 articles about (3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one 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: 93.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 371784-99-5
(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8-tetramethyl-undecan-5-one

: 371785-00-1
(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 - 25 ℃; for 1h;
DOI:10.1021/ja011338b

Reference yield:

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

: 371785-00-1
(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one

Guidance literature:: Multi-step reaction with 12 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: 1.60 g / Ag₂O; TBAI / toluene / 24 h / 25 - 50 °C

9.1: 516 mg / TBAF / tetrahydrofuran / 4 h / 25 °C

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

11.1: LDA / tetrahydrofuran / 1.5 h / -78 - -40 °C

11.2: 979 mg / tetrahydrofuran / 0.07 h / -78 °C

12.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 - 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; 1,2-dimethoxyethane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; iodine; diethylzinc; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; 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; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: Charette cyclopropanation;
DOI:10.1021/ja011338b

Reference yield:

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

: 371785-00-1
(3S,6R,7S,8S)-11-((1S,2R)-2-Benzyloxymethyl-cyclopropyl)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8-tetramethyl-undecan-5-one

Guidance literature:: Multi-step reaction with 10 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: 1.60 g / Ag₂O; TBAI / toluene / 24 h / 25 - 50 °C

7.1: 516 mg / TBAF / tetrahydrofuran / 4 h / 25 °C

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

9.1: LDA / tetrahydrofuran / 1.5 h / -78 - -40 °C

9.2: 979 mg / tetrahydrofuran / 0.07 h / -78 °C

10.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 - 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; 1,2-dimethoxyethane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; iodine; diethylzinc; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; 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; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 5.1: Charette cyclopropanation;
DOI:10.1021/ja011338b