(1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl ester
• CAS No.: 227002-20-2
• Molecular Formula: C₁₄H₂₇NO₆Si
• Molecular Weight: 333.457

Synonyms:(1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl ester

Chemical Property of (1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl ester

There total 2 articles about (1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl 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: 92.0%

(1R,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-oxo-cyclohexanecarboxylic acid methyl ester (227002-16-6) → (1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl ester (227002-20-2)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1021/jo990004q

Reference yield:

(1R,3R,4S)-4-(tert-butyldimethylsiloxy)-1-hydroxy-5-oxocyclohexane-1,3-carbolactone (189366-37-8) → (1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl ester (227002-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / NaOMe / 1 h / 20 °C

2: 92 percent / aq. OHNH₃Cl, NaOAc / acetonitrile / 16 h / 20 °C

With hydroxylamine hydrochloride; sodium methylate; sodium acetate; In acetonitrile;

DOI:10.1021/jo990004q

Reference yield:

(1S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-[(E)-hydroxyimino]-cyclohexanecarboxylic acid methyl ester (227002-20-2) → methyl (1S,3E,4R,5R)-3-(hydroxyimino)-1,4,5-trihydroxycyclohexane-1-carboxylate (494211-81-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/jo990004q

upstream raw materials:

(1R,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-1,4-dihydroxy-5-oxo-cyclohexanecarboxylic acid methyl ester

(1R,3R,4S)-4-(tert-butyldimethylsiloxy)-1-hydroxy-5-oxocyclohexane-1,3-carbolactone

Downstream raw materials:

methyl (1S,3E,4R,5R)-3-(hydroxyimino)-1,4,5-trihydroxycyclohexane-1-carboxylate

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