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

Base Information

Chemical Name:methyl (3S,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-cyclohex-1-enecarboxylate
CAS No.:262594-23-0
Molecular Formula:C₁₄H₂₆O₄Si
Molecular Weight:286.444
Hs Code.:

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

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

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

There total 7 articles about methyl (3S,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-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%

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

: 262594-23-0
methyl (3S,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-cyclohex-1-enecarboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(99)02152-8

Reference yield:

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

: 262594-23-0
methyl (3S,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / pyridine; POCl₃ / 10 h / 20 °C

2: 84 percent / TBAF / tetrahydrofuran / 15 h / 0 °C

With pyridine; tetrabutyl ammonium fluoride; trichlorophosphate; In tetrahydrofuran; 1: Dehydration / 2: Dehydration;
DOI:10.1021/jo000443l

Reference yield:

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

: 262594-23-0
methyl (3S,5R)-5-[(tert-butyldimethylsilyl)oxy]-3-hydroxy-cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 6 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

6: 84 percent / TBAF / tetrahydrofuran / 15 h / 0 °C

With pyridine; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Methylation / 2: silylation / 3: thioacylation / 4: dethiocarboxylation / 5: Dehydration / 6: Dehydration;
DOI:10.1021/jo000443l