(2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide

Base Information

• Chemical Name: (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide
• CAS No.: 141964-95-6
• Molecular Formula: C₂₀H₃₅NO₅Si
• Molecular Weight: 397.587

Synonyms:(2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide

Chemical Property of (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide

There total 3 articles about (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide 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: 88.0%

N-methoxylamine hydrochloride (593-56-6) + (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-butyric acid methyl ester (141964-93-4) → (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide (141964-95-6)

Guidance literature:

With trimethylaluminum; In toluene; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)91648-4

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide (141964-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

2: 88 percent / Me₃Al / toluene / 2 h / Ambient temperature

With 1H-imidazole; trimethylaluminum; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)91648-4

Reference yield:

(2R,3S)-4-Benzyloxy-3-hydroxy-2-((R)-1-hydroxy-ethyl)-butyric acid methyl ester (141964-92-3,142035-37-8,142035-38-9,142035-39-0) → (2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-N-methoxy-butyramide (141964-95-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

2: 88 percent / Me₃Al / toluene / 2 h / Ambient temperature

With 1H-imidazole; trimethylaluminum; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)91648-4

upstream raw materials:

N-methoxylamine hydrochloride

(2S,3S)-4-Benzyloxy-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-butyric acid methyl ester

tert-butyldimethylsilyl chloride

(2R,3S)-4-Benzyloxy-3-hydroxy-2-((R)-1-hydroxy-ethyl)-butyric acid methyl ester

Downstream raw materials:

(3S,4R)-4-Benzyloxymethyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

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