methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate

Base Information

Chemical Name:methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate
CAS No.:262594-22-9
Molecular Formula:C₂₀H₄₀O₄Si₂
Molecular Weight:400.706
Hs Code.:

Synonyms:methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate

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Technology Process of methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate

There total 10 articles about methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate 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: 84.0%

: methyl (3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-[(imidazoylthiocarbonyl)oxy]cyclohex-1-enecarboxylate

: 262594-22-9
methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate

Guidance literature:: With potassium dihydrogenphosphate; 2,2'-azobis(isobutyronitrile); triethylamine; In 1,2-dimethoxyethane; for 2h; Reflux;

Reference yield: 80.0%

: 139356-33-5
(3S,5S)-3,5-bis[(tert-butyl)dimethylsilyloxy]-1-hydroxycyclohexane-1-carboxylic acid methyl ester

: 262594-22-9
methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate

Guidance literature:: With pyridine; trichlorophosphate;
DOI:10.1016/S0040-4039(99)02152-8

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 262594-22-9
methyl (3S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / HCl / 6 h / 60 °C

2: 74 percent / Et₃N / dimethylformamide / 16 h / 20 °C

3: 83 percent / CH₂Cl₂ / 120 h / 20 °C

4: 93 percent / Bu₃SnH; AIBN / toluene / 2 h / 85 °C

5: 80 percent / pyridine; POCl₃ / 10 h / 20 °C

With pyridine; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; trichlorophosphate; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Methylation / 2: silylation / 3: thioacylation / 4: dethiocarboxylation / 5: Dehydration;
DOI:10.1021/jo000443l