N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine

Base Information

• Chemical Name: N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine
• CAS No.: 339533-60-7
• Molecular Formula: C₅₅H₉₀N₂O₅Si₂
• Molecular Weight: 915.501

Synonyms:N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine

Chemical Property of N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine

There total 29 articles about N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine 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:

2-ethyl-1,3-propandiol (2612-29-5) → N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine (339533-60-7)

Guidance literature:

Multi-step reaction with 18 steps

1.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

1.2: 100 percent / tetrahydrofuran; various solvent(s) / 1 h / -30 °C

2.1: 48 percent / Lipase PS₃O / pentane / 24 h / 20 °C

3.1: 90 percent / K₂CO₃ / methanol / 13 h / 20 °C

4.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: LiN(Me₃Si)2 / tetrahydrofuran / 0.33 h / -10 - 20 °C

5.2: 7.63 g / tetrahydrofuran / 0.5 h / 0 °C

6.1: 83 percent / aq. HF / acetonitrile; CH₂Cl₂ / 2 h / 20 °C

7.1: 85 percent / imidazole / dimethylformamide / 14 h / -5 - 20 °C

8.1: H₂ / Pd/C; TFA / ethanol / 12 h / 760.05 Torr

9.1: 71 percent / DIBAL-H / tetrahydrofuran / 6.75 h / -78 - -50 °C

10.1: 90 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 25 °C

11.1: 89 percent / TMSOTf / CH₂Cl₂ / 37 h / -78 - -55 °C

12.1: O₃ / pyridine / methanol / -78 °C

12.2: 89 percent / Me₂S / methanol / 12 h / -78 - 20 °C

13.1: 95 percent / TiCl₄ / CH₂Cl₂ / 37 h / -78 - -20 °C

14.1: BCl₃*SMe₂ / CH₂Cl₂ / 16 h / -78 - -10 °C

15.1: p-TsOH / 8 h / 20 °C

16.1: O₃ / pyridine / methanol / -78 °C

16.2: 1.66 g / Me₂S / methanol / 12 h / -78 - 20 °C

17.1: 3.1 g / TMSCl / 15 h / 0 - 25 °C

18.1: LDA / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

18.2: 3.2 g / tetrahydrofuran; various solvent(s) / 6 h / 0 °C

With 1H-imidazole; n-butyllithium; chloro-trimethyl-silane; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; boron trichloride - methyl sulfide complex; Lipase PS₃O; hydrogen fluoride; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; pyridine; palladium on activated charcoal; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane;

DOI:10.1021/jo001767c

Reference yield:

2-(((tert-butyldimethylsilyl)oxy)methyl)butan-1-ol (131899-18-8) → N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine (339533-60-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 48 percent / Lipase PS₃O / pentane / 24 h / 20 °C

2.1: 90 percent / K₂CO₃ / methanol / 13 h / 20 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: LiN(Me₃Si)2 / tetrahydrofuran / 0.33 h / -10 - 20 °C

4.2: 7.63 g / tetrahydrofuran / 0.5 h / 0 °C

5.1: 83 percent / aq. HF / acetonitrile; CH₂Cl₂ / 2 h / 20 °C

6.1: 85 percent / imidazole / dimethylformamide / 14 h / -5 - 20 °C

7.1: H₂ / Pd/C; TFA / ethanol / 12 h / 760.05 Torr

8.1: 71 percent / DIBAL-H / tetrahydrofuran / 6.75 h / -78 - -50 °C

9.1: 90 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 25 °C

10.1: 89 percent / TMSOTf / CH₂Cl₂ / 37 h / -78 - -55 °C

11.1: O₃ / pyridine / methanol / -78 °C

11.2: 89 percent / Me₂S / methanol / 12 h / -78 - 20 °C

12.1: 95 percent / TiCl₄ / CH₂Cl₂ / 37 h / -78 - -20 °C

13.1: BCl₃*SMe₂ / CH₂Cl₂ / 16 h / -78 - -10 °C

14.1: p-TsOH / 8 h / 20 °C

15.1: O₃ / pyridine / methanol / -78 °C

15.2: 1.66 g / Me₂S / methanol / 12 h / -78 - 20 °C

16.1: 3.1 g / TMSCl / 15 h / 0 - 25 °C

17.1: LDA / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

17.2: 3.2 g / tetrahydrofuran; various solvent(s) / 6 h / 0 °C

With 1H-imidazole; chloro-trimethyl-silane; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; boron trichloride - methyl sulfide complex; Lipase PS₃O; hydrogen fluoride; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; pyridine; palladium on activated charcoal; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane;

DOI:10.1021/jo001767c

Reference yield:

ethyl diethyl malonate (133-13-1) → N'-[7-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-(1-{6-[3-(tert-butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-octylidene]-N,N-dimethyl-hydrazine (339533-60-7)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 65 percent / LiAlH₄ / tetrahydrofuran / 13 h / Heating

2.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

2.2: 100 percent / tetrahydrofuran; various solvent(s) / 1 h / -30 °C

3.1: 48 percent / Lipase PS₃O / pentane / 24 h / 20 °C

4.1: 90 percent / K₂CO₃ / methanol / 13 h / 20 °C

5.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: LiN(Me₃Si)2 / tetrahydrofuran / 0.33 h / -10 - 20 °C

6.2: 7.63 g / tetrahydrofuran / 0.5 h / 0 °C

7.1: 83 percent / aq. HF / acetonitrile; CH₂Cl₂ / 2 h / 20 °C

8.1: 85 percent / imidazole / dimethylformamide / 14 h / -5 - 20 °C

9.1: H₂ / Pd/C; TFA / ethanol / 12 h / 760.05 Torr

10.1: 71 percent / DIBAL-H / tetrahydrofuran / 6.75 h / -78 - -50 °C

11.1: 90 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 25 °C

12.1: 89 percent / TMSOTf / CH₂Cl₂ / 37 h / -78 - -55 °C

13.1: O₃ / pyridine / methanol / -78 °C

13.2: 89 percent / Me₂S / methanol / 12 h / -78 - 20 °C

14.1: 95 percent / TiCl₄ / CH₂Cl₂ / 37 h / -78 - -20 °C

15.1: BCl₃*SMe₂ / CH₂Cl₂ / 16 h / -78 - -10 °C

16.1: p-TsOH / 8 h / 20 °C

17.1: O₃ / pyridine / methanol / -78 °C

17.2: 1.66 g / Me₂S / methanol / 12 h / -78 - 20 °C

18.1: 3.1 g / TMSCl / 15 h / 0 - 25 °C

19.1: LDA / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

19.2: 3.2 g / tetrahydrofuran; various solvent(s) / 6 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; boron trichloride - methyl sulfide complex; Lipase PS₃O; hydrogen fluoride; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; pyridine; palladium on activated charcoal; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane;

DOI:10.1021/jo001767c

upstream raw materials:

[(1S,3R)-3-Benzyloxy-1-((R)-2-iodo-1-methyl-ethyl)-butoxy]-tert-butyl-dimethyl-silane

N'-[(S)-2-{(4S,5R,6S)-6-[(R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-pentyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-1-methyl-prop-(E)-ylidene]-N,N-dimethyl-hydrazine

(E)-(R)-4-Hydroxymethyl-hex-2-enoic acid methyl ester

(R)-2-((tert-butyldimethylsilyloxy)methyl)butan-1-ol

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