(S)-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-(methanesulfonyloxy)propane

Base Information

Chemical Name:(S)-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-(methanesulfonyloxy)propane
CAS No.:685142-98-7
Molecular Formula:C₂₇H₃₅NO₇SSi
Molecular Weight:545.729
Hs Code.:

Synonyms:(S)-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-(methanesulfonyloxy)propane

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

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

There total 13 articles about (S)-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-(methanesulfonyloxy)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: 93.0%

: 124-63-0
methanesulfonyl chloride

: 685142-97-6
(R)-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)propan-1-ol

: 685142-98-7
(S)-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-(methanesulfonyloxy)propane

Guidance literature:: With pyridine; at 0 - 25 ℃; for 2h;
DOI:10.1021/jo035465x

Reference yield:

: 5959-56-8
4-amino-1-naphthol hydrochloride

: 685142-98-7
(S)-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-(methanesulfonyloxy)propane

Guidance literature:: Multi-step reaction with 13 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: 88 percent / 4 Angstroem molecular sieves; Pseudomonas sp. lipase / 20 h / 35 °C

11.1: 70 percent / imidazole / dimethylformamide / 2 h / 25 °C

12.1: 83 percent / MeOH; K₂CO₃ / 0.5 h / 25 °C

13.1: 93 percent / pyridine / 2 h / 0 - 25 °C

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

Reference yield:

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

: 685142-98-7
(S)-2-(4-benzyloxy-2-nitronaphthalen-1-yl)-3-(tert-butyldimethylsilyloxy)-1-(methanesulfonyloxy)propane

Guidance literature:: Multi-step reaction with 10 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

9.1: 83 percent / MeOH; K₂CO₃ / 0.5 h / 25 °C

10.1: 93 percent / pyridine / 2 h / 0 - 25 °C

With pyridine; 1H-imidazole; methanol; 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