Carbamic acid, [1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(hydroxymethyl)ethyl]- 4-(phenylmethoxy)-2-naphthalenyl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, [1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(hydroxymethyl)ethyl]- 4-(phenylmethoxy)-2-naphthalenyl]-, 1,1-dimethylethyl ester
• CAS No.: 685143-07-1
• Molecular Formula: C₃₁H₄₃NO₅Si
• Molecular Weight: 537.772

Synonyms:

Chemical Property of Carbamic acid, [1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(hydroxymethyl)ethyl]- 4-(phenylmethoxy)-2-naphthalenyl]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(hydroxymethyl)ethyl]- 4-(phenylmethoxy)-2-naphthalenyl]-, 1,1-dimethylethyl ester

There total 17 articles about Carbamic acid, [1-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(hydroxymethyl)ethyl]- 4-(phenylmethoxy)-2-naphthalenyl]-, 1,1-dimethylethyl 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:

4-acetoxy-1-(acetylamino)-2-nitronaphthalene (20032-84-2) → (R)-2-(4-benzyloxy-2-(tert-butyloxycarbonylamino)naphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-propanol (685143-07-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 99 percent / MeOH; K₂CO₃ / 0.5 h / 0 °C

2.1: 92 percent / Bu₄NI; K₂CO₃ / dimethylformamide / 1.25 h / 25 °C

3.1: 78 percent / NaOH / methanol / 3 h / 70 °C

4.1: 76 percent / BF₃*OEt₂; t-BuONO / 1,2-dimethoxy-ethane / 2 h / -15 - 0 °C

5.1: 75 percent / CuCl; CuCl₂ / H₂O; acetonitrile / 0 - 25 °C

6.1: NaH / dimethylformamide / 0.5 h / 0 °C

6.2: 86 percent / dimethylformamide / 12 h / 80 °C

7.1: 76 percent / BH₃*SMe₂ / dioxane / 16 h / 70 °C

8.1: 62 percent / p-TsOH / dimethylformamide / 16 h / 25 °C

9.1: 68 percent / H₂ / Pd/CaCO₃ poisoned with lead and quinoline / ethyl acetate / 8 h / 25 °C

10.1: 80 percent / tetrahydrofuran / 24 h / 70 °C

11.1: 88 percent / MeOH; p-TsOH / 1 h / 25 °C

12.1: 4 Angstroem molecular sieves; Pseudomonas sp. lipase / 43 h / 35 °C

13.1: imidazole / dimethylformamide / 2 h / 25 °C

14.1: MeOH; K₂CO₃ / 0.5 h / 25 °C

With 1H-imidazole; methanol; sodium hydroxide; tert.-butylnitrite; Pseudomonas sp. lipase; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; copper(l) chloride; copper dichloride; quinoline; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo035465x

Reference yield:

4-acetoxy-1-(acetylamino)naphthalene (98728-71-3) → (R)-2-(4-benzyloxy-2-(tert-butyloxycarbonylamino)naphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-propanol (685143-07-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 78 percent / HNO₃ / 1 h / 18 °C

2.1: 99 percent / MeOH; K₂CO₃ / 0.5 h / 0 °C

3.1: 92 percent / Bu₄NI; K₂CO₃ / dimethylformamide / 1.25 h / 25 °C

4.1: 78 percent / NaOH / methanol / 3 h / 70 °C

5.1: 76 percent / BF₃*OEt₂; t-BuONO / 1,2-dimethoxy-ethane / 2 h / -15 - 0 °C

6.1: 75 percent / CuCl; CuCl₂ / H₂O; acetonitrile / 0 - 25 °C

7.1: NaH / dimethylformamide / 0.5 h / 0 °C

7.2: 86 percent / dimethylformamide / 12 h / 80 °C

8.1: 76 percent / BH₃*SMe₂ / dioxane / 16 h / 70 °C

9.1: 62 percent / p-TsOH / dimethylformamide / 16 h / 25 °C

10.1: 68 percent / H₂ / Pd/CaCO₃ poisoned with lead and quinoline / ethyl acetate / 8 h / 25 °C

11.1: 80 percent / tetrahydrofuran / 24 h / 70 °C

12.1: 88 percent / MeOH; p-TsOH / 1 h / 25 °C

13.1: 4 Angstroem molecular sieves; Pseudomonas sp. lipase / 43 h / 35 °C

14.1: imidazole / dimethylformamide / 2 h / 25 °C

15.1: MeOH; K₂CO₃ / 0.5 h / 25 °C

With 1H-imidazole; methanol; sodium hydroxide; tert.-butylnitrite; Pseudomonas sp. lipase; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; nitric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; copper(l) chloride; copper dichloride; quinoline; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo035465x

Reference yield:

4-amino-1-naphthol hydrochloride (5959-56-8) → (R)-2-(4-benzyloxy-2-(tert-butyloxycarbonylamino)naphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-propanol (685143-07-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 84 percent / Et₃N / CH₂Cl₂ / 3.5 h / 0 °C

2.1: 78 percent / HNO₃ / 1 h / 18 °C

3.1: 99 percent / MeOH; K₂CO₃ / 0.5 h / 0 °C

4.1: 92 percent / Bu₄NI; K₂CO₃ / dimethylformamide / 1.25 h / 25 °C

5.1: 78 percent / NaOH / methanol / 3 h / 70 °C

6.1: 76 percent / BF₃*OEt₂; t-BuONO / 1,2-dimethoxy-ethane / 2 h / -15 - 0 °C

7.1: 75 percent / CuCl; CuCl₂ / H₂O; acetonitrile / 0 - 25 °C

8.1: NaH / dimethylformamide / 0.5 h / 0 °C

8.2: 86 percent / dimethylformamide / 12 h / 80 °C

9.1: 76 percent / BH₃*SMe₂ / dioxane / 16 h / 70 °C

10.1: 62 percent / p-TsOH / dimethylformamide / 16 h / 25 °C

11.1: 68 percent / H₂ / Pd/CaCO₃ poisoned with lead and quinoline / ethyl acetate / 8 h / 25 °C

12.1: 80 percent / tetrahydrofuran / 24 h / 70 °C

13.1: 88 percent / MeOH; p-TsOH / 1 h / 25 °C

14.1: 4 Angstroem molecular sieves; Pseudomonas sp. lipase / 43 h / 35 °C

15.1: imidazole / dimethylformamide / 2 h / 25 °C

16.1: MeOH; K₂CO₃ / 0.5 h / 25 °C

With 1H-imidazole; methanol; sodium hydroxide; tert.-butylnitrite; Pseudomonas sp. lipase; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; nitric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; copper(l) chloride; copper dichloride; quinoline; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo035465x

upstream raw materials:

(R)-1-acetoxy-2-(4-benzyloxy-2-(tert-butyloxycarbonylamino)naphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane

di-tert-butyl dicarbonate

4-acetoxy-1-(acetylamino)-2-nitronaphthalene

4-acetoxy-1-(acetylamino)naphthalene

Downstream raw materials:

(R)-5-benzyloxy-1-(tert-butyldimethylsilyloxymethyl)-3-(tert-butyloxycarbonyl)-2,3-dihydro-1H-benz[e]indole

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