(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Base Information

• Chemical Name: (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
• CAS No.: 552298-37-0
• Molecular Formula: C₃₀H₄₅NO₃
• Molecular Weight: 467.692
• Mol file: 552298-37-0.mol

Synonyms:(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Chemical Property of (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

There total 1 articles about (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 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: 89.0%

(1R,2R)-(-)-pseudoephedrinepropionamide (192060-67-6) + ((2S,4R,6R)-7-Iodo-2,4,6-trimethyl-heptyloxymethyl)-benzene (552298-26-7) → (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (552298-37-0)

Guidance literature:

With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 18h;

DOI:10.1002/anie.200460203

Reference yield: 92.0%

(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (552298-37-0) → (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonan-1-ol (768395-17-1)

Guidance literature:

With lithium amidotrihydroborate; In dichloromethane; at -78 - 0 ℃; for 3h;

DOI:10.1002/anie.200460203

Reference yield:

(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (552298-37-0) → borrelidin (7184-60-3,97328-74-0)

Guidance literature:

Multi-step reaction with 22 steps

1.1: 92 percent / LiNH₂*BH₃ / CH₂Cl₂ / 3 h / -78 - 0 °C

2.1: 95 percent / imidazole; DMAP / 8 h / 25 °C

3.1: 87 percent / H₂ / Pd/C / ethanol / 12 h / 25 °C

4.1: NaH / tetrahydrofuran / 1 h

4.2: 85 percent / TBAI / tetrahydrofuran / 12 h / 25 °C

5.1: 93 percent / TBAF / tetrahydrofuran / 12 h / 25 °C

6.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

7.1: n-BuLi / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 0.5 h / -78 °C

7.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C

8.1: Ph₂S / sunlight

9.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

10.1: 89 percent / DDQ / H₂O; CH₂Cl₂ / 0.5 h / 25 °C / pH 7.0

11.1: 94 percent / TEMPO; bis(acetoxy)iodobenzene / CH₂Cl₂ / 2 h / 25 °C

12.1: BF₃*OEt₂ / tetrahydrofuran / 1 h / -78 °C

13.1: 86 percent / iPr₂NEt / CH₂Cl₂ / 12 h / 25 °C

14.1: 88 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C

15.1: 83 percent / CF₃COOH / CH₂Cl₂ / 3 h / 0 °C

16.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 25 °C

16.2: 59 percent / DMAP / tetrahydrofuran; toluene / 12 h / 25 °C

17.1: hydroquinone; nBu₃SnH / Mo(CO)3(tBuNC)3 / tetrahydrofuran / 12 h / 55 °C

17.2: 54 percent / I₂ / CH₂Cl₂ / 25 °C

18.1: 90 percent / CuI / Pd(PPh₃)4 / toluene / 8 h / 80 °C

19.1: 69 percent / Me₂BBr / CH₂Cl₂ / 2 h / -78 °C

20.1: 85 percent / TEMPO; TCCA / CH₂Cl₂ / 1 h / 25 °C

21.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 0.5 h / 25 °C

22.1: NaBH₄; CeCl₃*7H₂O / methanol / 1 h / 0 °C

With 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; n-butyllithium; cerium(III) chloride; 2-methyl-but-2-ene; dimethylboron bromide; [bis(acetoxy)iodo]benzene; diphenyl sulfide; lithium amidotrihydroborate; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; hydroquinone; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Mo(CO)3(CN-t-Bu)3; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 6.1: Dess-Martin oxidation / 9.1: Dess-Martin oxidation / 12.1: Mukaiyama reaction / 16.1: Yamaguchi reaction / 22.1: Luche reaction;

DOI:10.1002/anie.200460203

upstream raw materials:

(1R,2R)-(-)-pseudoephedrinepropionamide

((2S,4R,6R)-7-Iodo-2,4,6-trimethyl-heptyloxymethyl)-benzene

Downstream raw materials:

(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonan-1-ol

borrelidin

(2S,4R,6S,8S)-9-[(4-methoxybenzyl)oxy]-2,4,6,8-tetramethylnonanal

(2S,4R,6S,8S)-9-[(4-methoxybenzyl)oxy]-2,4,6,8-tetramethylnonan-1-ol