(4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 148694-46-6
• Molecular Formula: C₂₀H₃₈O₅Si₂
• Molecular Weight: 414.69

Synonyms:(4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property of (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

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Technology Process of (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester

There total 2 articles about (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic 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: 94.0%

methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate (84806-48-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester (148694-46-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 12h; Ambient temperature;

DOI:10.1021/jo00116a023

Reference yield:

(-)-3-dehydroshikimic acid (2922-42-1) → (4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester (148694-46-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / -40 °C

2: imidazole / dimethylformamide

With 1H-imidazole; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1055/s-1996-4440

Reference yield: 89.0%

(4S,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester (148694-46-6) → methyl [3S-(3α,4β,5α)]-4,5-bis{[(1,1-dimethylethyl)dimethylsilyl]oxy}-3-hydroxy-1-cyclohexene-1-carboxylate (163563-65-3)

Guidance literature:

With lithium tri(t-butoxy)aluminum hydride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jo00116a023

upstream raw materials:

methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate

tert-butyldimethylsilyl chloride

(-)-3-dehydroshikimic acid

Downstream raw materials:

(4R,5R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methylene-cyclohex-1-enecarboxylic acid methyl ester

methyl [3S-(3α,4β,5α)]-4,5-bis{[(1,1-dimethylethyl)dimethylsilyl]oxy}-3-hydroxy-1-cyclohexene-1-carboxylate

(4R,5R)-4,5-Dihydroxy-3-methylene-cyclohex-1-enecarboxylic acid methyl ester

methyl 3-homoshikimate

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