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

Base Information

Chemical Name:(R)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane
CAS No.:685142-96-5
Molecular Formula:C₂₈H₃₅NO₆Si
Molecular Weight:509.675
Hs Code.:

Synonyms:(R)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane

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Chemical Property of (R)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane

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Technology Process of (R)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane

There total 9 articles about (R)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane 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: 70.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 685142-90-9
(S)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)propan-3-ol

: 685142-96-5
(R)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 2h;
DOI:10.1021/jo035465x

Reference yield:

: 685143-09-3
1-(acetylamino)-4-hydroxy-2-nitronaphthalene

: 685142-96-5
(R)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane

Guidance literature:: Multi-step reaction with 8 steps

1.1: 92 percent / Bu₄NI; K₂CO₃ / dimethylformamide / 1.25 h / 25 °C

2.1: 78 percent / NaOH / methanol / 3 h / 70 °C

3.1: 76 percent / BF₃*OEt₂; t-BuONO / 1,2-dimethoxy-ethane / 2 h / -15 - 0 °C

4.1: 75 percent / CuCl; CuCl₂ / H₂O; acetonitrile / 0 - 25 °C

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

5.2: 86 percent / dimethylformamide / 12 h / 80 °C

6.1: 76 percent / BH₃*SMe₂ / dioxane / 16 h / 70 °C

7.1: 88 percent / 4 Angstroem molecular sieves; Pseudomonas sp. lipase / 20 h / 35 °C

8.1: 70 percent / imidazole / dimethylformamide / 2 h / 25 °C

With 1H-imidazole; sodium hydroxide; tert.-butylnitrite; Pseudomonas sp. lipase; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; copper(l) chloride; copper dichloride; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo035465x

Reference yield:

: 685142-86-3
4-benzyloxy-1-chloro-2-nitronaphthalene

: 685142-96-5
(R)-1-acetoxy-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propane

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 86 percent / dimethylformamide / 12 h / 80 °C

2.1: 76 percent / BH₃*SMe₂ / dioxane / 16 h / 70 °C

3.1: 88 percent / 4 Angstroem molecular sieves; Pseudomonas sp. lipase / 20 h / 35 °C

4.1: 70 percent / imidazole / dimethylformamide / 2 h / 25 °C

With 1H-imidazole; Pseudomonas sp. lipase; dimethylsulfide borane complex; 4 A molecular sieve; sodium hydride; In 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1021/jo035465x